4-Aminobenzonitrile → HCID 67040913, compound

HRID 605279Notes

Reaction equation

HRID 605279 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].[NH2:33][C:34]1[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=1.NC1C=C(O)C(C)=CC=1>CO>[C:38]([C:37]1[CH:40]=[CH:41][C:34]([NH:33][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]([CH3:2])[CH3:3])=[N:32][C:8]=4[N:9]=[CH:10][N:11]=3)[CH:15]=2)=[CH:35][CH:36]=1)#[N:39]

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 178185-Amino-2-methylphenolHCID 866155503-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chloride

Product 1

HCID 67040913HCID 67040913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 137B was reacted with 4-aminobenzonitrile according to the procedure from Example 137C substituting 4-aminobenzyonitrile for 5-amino-o-cresol to provide the title compound as an off white solid after trituration of the reaction product from methanol (20 mg, 23%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 10.63 (s, 1 H), 8.92 (s, 1 H), 8.69 (s, 1 H), 7.96 (d, J=8.82 Hz, 2 H), 7.66-7.90 (m, 4 H), 7.35-7.46 (m, 3 H), 6.95-7.11 (m, 3 H), 6.55-6.64 (m, 1 H), 3.77 (s, 3 H), 3.18-3.30 (m, 1 H), 1.35 (d, J=6.99 Hz, 6 H); MS (ESI+) m/z 547.3 (M+H)+, (ESI−) m/z 545.3 (M−H)−.

Sources & evidence

ORD record
ord-b054efb8c4a34111a4bc1751e115004a
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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