3-Bromoaniline → HCID 67040336, compound

HRID 605172Notes

Reaction equation

HRID 605172 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C:17](Cl)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:32]=1)([CH3:3])[CH3:2].[Br:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37].NC1C=C(O)C(C)=CC=1>>[Br:33][C:34]1[CH:35]=[C:36]([NH:37][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:22]([S:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[C:14]([NH:13][C:12]3[C:7]4[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[N:32][C:8]=4[N:9]=[CH:10][N:11]=3)[CH:15]=2)[CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 3

HCID 115623-BromoanilineHCID 178185-Amino-2-methylphenolHCID 866155503-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chloride

Product 1

HCID 67040336HCID 67040336, compound

Procedure

The product from Example 137B was reacted with 3-bromoaniline according to the procedure from Example 137C substituting 3-bromoaniline for 5-amino-o-cresol to provide the title compound as an off white solid after silica gel chromatography (50 mg, 38%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6H), 3.16-3.30 (m, 1H), 3.77 (s, 3H), 7.00 (d, J=8.82 Hz, 2H), 7.40 (d, J=8.82 Hz, 2H), 7.53 (d, J=8.82 Hz, 2H), 7.64 (d, J=8.82 Hz, 1), 7.74 (d, J=8.82 Hz, 2H), 7.81 (dd, J=8.46, 1.84 Hz, 1H), 7.99 (d, J=1.47 Hz, 1H), 8.59 (s, 1H), 8.86 (d, J=8.82 Hz, 1H), 10.21 (s, 1H), 10.33 (s, 1H); MS (APCI) m/z 602 (M+H)+.

Sources & evidence

ORD record
ord-365e1e68a41e4bf6ac856bd5a9ffd2df
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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