Diisopropylethylamine → HCID 71246899, compound

HRID 715066Notes

Reaction equation

HRID 715066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=2)[NH2:9])=[CH:4][C:3]=1[F:16].CCN(C(C)C)C(C)C.[OH:26][CH2:27][C@@H:28]([NH:30][C:31]1[N:40]=[CH:39][C:38]2[C:33](=[CH:34][C:35]([C:41](O)=[O:42])=[CH:36][CH:37]=2)[N:32]=1)[CH3:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=2)[NH:9][C:41]([C:35]2[CH:34]=[C:33]3[C:38]([CH:39]=[N:40][C:31]([NH:30][C@@H:28]([CH3:29])[CH2:27][OH:26])=[N:32]3)=[CH:37][CH:36]=2)=[O:42])=[CH:4][C:3]=1[F:16]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68294236HCID 68294236, compoundHCID 71247482HCID 71247482, compound

Product 1

HCID 71246899HCID 71246899, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the hydrochloride salt of 40c (140 mg, 0.506 mmol), and DIPEA (88.1 μL, 0.506 mmol) and DMF (5 mL) under nitrogen was added 70 (125 mg, 0.506 mmol) and HBTU (211 mg, 0.556 mmol) and the reaction was stirred at RT for 18 h. The reaction was poured into water and extracted with EtOAc. The combined extracts were dried (MgSO4) and evaporated and the crude material was purified by reverse phase chromatography (SP4) eluting with a MeCN/H2O gradient (10 to 95% MeCN) to afford 83.5 mg (35.2%) of N-((4-chloro-3-fluorophenyl)(1-methyl-1H-pyrazol-4-yl)methyl)-2-((S)-1-hydroxypropan-2-ylamino)quinazoline-7-carboxamide (I-1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customthe crude material was purified by reverse phase chromatography (SP4)
  5. washeluting with a MeCN/H2O gradient (10 to 95% MeCN)

Sources & evidence

ORD record
ord-1956c79538954166b1ebfe5204da9b28
Source dataset
uspto-grants-2015_11
Patent number
US09187462B2

Reaction notes

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