Ammonium Hydroxide → 8-(5-Aminopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

HRID 20688

Reaction equation

HRID 20688 reaction equation
[NH4+:1].[OH-].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([O:30][CH3:31])=[CH:12][CH:13]=[C:14]2[C:19]=1[O:18][C:17](=[O:20])[CH:16]=[C:15]2[NH:21][C:22]1[C:27]([Cl:28])=[CH:26][N:25]=[CH:24][C:23]=1[Cl:29]>>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([O:30][CH3:31])=[CH:12][CH:13]=[C:14]2[C:19]=1[O:18][C:17](=[O:20])[CH:16]=[C:15]2[NH:21][C:22]1[C:27]([Cl:28])=[CH:26][N:25]=[CH:24][C:23]=1[Cl:29]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 248495698-(5-Bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248498868-(5-Aminopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Procedure

The title compound was prepared from 28% NH4OH solution and 8-(5-bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (Example 28) following the procedure outlined in Example 52. 1H NMR (400 MHz, DMSO-d6; HCl salt): δ 9.64 (s, 1H), 8.81 (s, 2H), 8.00 (d, 1H), 7.83 (br, 3H), 7.21 (d, 1H), 4.63 (s, 1H), 3.98 (t, 2H), 3.92 (s, 3H), 2.79 (m, 2H), 1.75-1.50 (m, 6H); MS (ESI): 437.9.

Sources & evidence

ORD record
ord-92ede4a64a14441ab8ac910e5ee5345c
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Linked notes

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