Diisopropylamine → HCID 178467687, compound

HRID 575414Notes

Reaction equation

HRID 575414 reaction equation
Br[C:2]1[CH:3]=[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:27]1[CH:32]=[CH:31][CH:30]=[N:29][C:28]=1[C@:33]([OH:37])([C:35]#[CH:36])[CH3:34].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]=[CH:3][C:2]([C:36]#[C:35][C@@:33]([OH:37])([C:28]6[N:29]=[CH:30][CH:31]=[CH:32][N:27]=6)[CH3:34])=[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 178513779HCID 178513779, compound

Product 1

HCID 178467687HCID 178467687, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-cyclopropyl-1H-1,2,4-triazol-5-yl)-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)-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 36.7 mg (41.6% yield). M+1=483.2. 1H NMR (400 MHz, DMSO-d6) δ 8.89 (d, J=4.8 Hz, 2H), 8.57 (d, J=2.2 Hz, 1H), 8.30 (br s, 1H), 7.72 (br s, 1H), 7.49 (t, J=4.8 Hz, 1H), 7.35 (dd, J=8.5, 2.3 Hz, 1H), 7.05 (d, J=8.5 Hz, 1H), 6.14 (s, 1H), 5.00-4.77 (m, 2H), 4.58-4.50 (m, 2H), 2.13-2.03 (m, 1H), 1.88 (s, 3H), 1.03-0.96 (m, 2H), 0.94-0.86 (m, 2H).

Workup

  1. customto afford 36.7 mg (41.6% yield)

Sources & evidence

ORD record
ord-ad3d6c7f542344658744bf66ad64158c
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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