Ammonia → HCID 58204559, compound

HRID 886143Notes

Reaction equation

HRID 886143 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([CH:25]([CH3:27])[CH3:26])[C:7]=1[C:8]1[N:9]=[C:10]2[C:16]3[CH:17]=[CH:18][C:19]([C:21](O)=[O:22])=[CH:20][C:15]=3[O:14][CH2:13][CH2:12][N:11]2[CH:24]=1)#[N:2].[NH3:28]>>[C:1]([C:3]1[CH:4]=[N:5][N:6]([CH:25]([CH3:27])[CH3:26])[C:7]=1[C:8]1[N:9]=[C:10]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]([NH2:28])=[O:22])=[CH:20][C:15]=3[O:14][CH2:13][CH2:12][N:11]2[CH:24]=1)#[N:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 582049342-[4-Cyano-1-(1-methylethyl)-1H-pyrazol-5-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxylic acid

Product 1

HCID 58204559HCID 58204559, compound

Procedure

Following Example 109, 2-(4-Cyano-1-isopropyl-1H-pyrazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylic acid from Example 16 was coupled with ammonia to give 138. Yield 27.8 mg (44%). MS (ESI): 363.1. 1H NMR (400 MHz, DMSO) δ 8.46 (d, J=8.4, 1H), 8.11 (s, 1H), 8.00 (d, J=4.7, 2H), 7.62 (dd, J=8.4, 1.5, 1H), 7.57 (d, J=1.4, 1H), 7.44 (s, 1H), 5.46 (dt, J=13.1, 6.5, 1H), 4.59 (dd, J=17.5, 4.8, 4H), 1.48 (d, J=6.6, 6H).

Sources & evidence

ORD record
ord-11ade629ba9443fc8f31d92edd6af7aa
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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