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Diisopropylethylamine → {1-[8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carbonyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester

HRID 2063767
Notes
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Reaction equation

HRID 2063767 reaction equation
C(N(C(C)C)CC)(C)C.[S:10]([C:14]1[CH:15]=[C:16]([NH:20][C:21]2[N:30]=[CH:29][C:28]3[CH:27]=[CH:26][C:25]4[N:31]=[C:32]([C:34]([OH:36])=O)[S:33][C:24]=4[C:23]=3[N:22]=2)[CH:17]=[CH:18][CH:19]=1)(=[O:13])(=[O:12])[NH2:11].[C:37]([O:41][C:42]([NH:44][CH:45]1[CH2:49][CH2:48][NH:47][CH2:46]1)=[O:43])([CH3:40])([CH3:39])[CH3:38].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C)C=O>[C:37]([O:41][C:42](=[O:43])[NH:44][CH:45]1[CH2:49][CH2:48][N:47]([C:34]([C:32]2[S:33][C:24]3[C:23]4[N:22]=[C:21]([NH:20][C:16]5[CH:17]=[CH:18][CH:19]=[C:14]([S:10](=[O:12])(=[O:13])[NH2:11])[CH:15]=5)[N:30]=[CH:29][C:28]=4[CH:27]=[CH:26][C:25]=3[N:31]=2)=[O:36])[CH2:46]1)([CH3:40])([CH3:38])[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 114864308-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acid

Product 1

HCID 59262801{1-[8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carbonyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester
Yield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (68 μl, 0.39 mmol) was added to a mixture of 8-(3-Sulfamoyl-phenylamino)-thiazolo[4,5-h]quinazoline-2-carboxylic acid (78 mg, 0.19 mmol), 3-(tert-butoxycarbonylamino)pyrrolidine (36.2 mg, 0.19 mmol) and PyBrop (91 mg, 0.19 mmol) in dimethylformamide (1 ml). The reaction mixture was stirred at room temperature for 12 h. The reaction was concentrated under reduced pressure, redissolved in isopropanol (˜10 mL) and water was added (˜5 mL). The precipitate formed was isolated by filtration and washed with water (1×5 mL), dilute NaHSO4 (1×5 mL), water (1×5 mL), saturated Na2CO3 (1×5 mL), water (1×5 mL), isopropanol (1×5 mL), diethyl ether (4×5 mL) giving a yellow powder (87 mg, 80% yield). MS (ES+) 570, (ES−) 568.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionredissolved in isopropanol (˜10 mL)
  3. additionwater was added (˜5 mL)
  4. customThe precipitate formed
  5. customwas isolated by filtration
  6. washwashed with water (1×5 mL), dilute NaHSO4 (1×5 mL), water (1×5 mL), saturated Na2CO3 (1×5 mL), water (1×5 mL), isopropanol (1×5 mL), diethyl ether (4×5 mL)

Sources & evidence

ORD record
ord-9c2ccf5eb096480ba13b2ac9548bec3d
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08288400B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes