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

HRID 643753Notes

Reaction equation

HRID 643753 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]

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 esterYield 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-bfcf4f9cdfad446988dc9b2833090b2d
Source dataset
uspto-grants-2010_04
Patent number
US07700609B2

Reaction notes

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