Diisopropylamine → HCID 178467679, compound

HRID 575412Notes

Reaction equation

HRID 575412 reaction equation
Br[C:2]1[C:3]([F:27])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]4[NH:22][N:21]=[C:20]([CH:23]5[CH2:25][CH2:24]5)[N:19]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[N:30][C:29]=1[C@:34]([OH:38])([C:36]#[CH:37])[CH3:35].C(NC(C)C)(C)C>CN(C=O)C>[CH:23]1([C:20]2[N:19]=[C:18]([C:12]3[N:8]4[CH2:9][CH2:10][O:11][C:5]5[CH:4]=[C:3]([F:27])[C:2]([C:37]#[C:36][C@@:34]([OH:38])([C:29]6[N:30]=[CH:31][CH:32]=[CH:33][N:28]=6)[CH3:35])=[CH:26][C:6]=5[C:7]4=[N:14][C:13]=3[C:15]([NH2:17])=[O:16])[NH:22][N:21]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 86693464(2R)-2-pyrimidin-2-ylbut-3-yn-2-olHCID 178513780HCID 178513780, compound

Product 1

HCID 178467679HCID 178467679, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-cyclopropyl-1H-1,2,4-triazol-5-yl)-9-fluoro-10-[(3R)-3-hydroxy-3-pyrimidin-2-yl-but-1-ynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was prepared similarly according to General Procedure E with slight modification. 10-bromo-3-(3-cyclopropyl-1H-1,2,4-triazol-5-yl)-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was reacted with (2R)-2-pyrimidin-2-ylbut-3-yn-2-ol in a solution of DMF (1.3 mL/mmol) and diisopropylamine (2.6 mL/mmol) to afford 47 mg of the titled compound (40% yield). M+1=501.2. 1H NMR (400 MHz, DMSO-d6) δ 8.89 (d, J=4.8 Hz, 2H), 8.64 (d, J=8.4 Hz, 1H), 8.35 (br s, 1H), 7.74 (br s, 1H), 7.50 (t, J=4.8 Hz, 1H), 7.03 (d, J=10.5 Hz, 1H), 6.21 (s, 1H), 5.04-4.80 (m, 2H), 4.63-4.54 (m, 2H), 2.13-2.04 (m, 1H), 1.89 (s, 3H), 1.03-0.95 (m, 2H), 0.93-0.87 (m, 2H).

Workup

  1. custom3-(3-cyclopropyl-1H-1,2,4-triazol-5-yl)-9-fluoro-10-[(3R)-3-hydroxy-3-pyrimidin-2-yl-but-1-ynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was prepared similarly

Sources & evidence

ORD record
ord-6023fc892bcd4a2f93aec8ea2090d63b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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