3-Methoxyaniline → HCID 67040273, compound

HRID 605174Notes

Reaction equation

HRID 605174 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].[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([NH2:41])[CH:36]=1.NC1C=C(O)C(C)=CC=1>>[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]([NH:41][C:37]3[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH3:33])[CH:36]=3)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:32]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 108243-MethoxyanilineHCID 178185-Amino-2-methylphenolHCID 866155503-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chloride

Product 1

HCID 67040273HCID 67040273, compound

Procedure

The product from Example 137B was reacted with m-anisidine according to the procedure from Example 137C substituting m-anisidine for 5-amino-o-cresol to provide the title compound as an off white solid after silica gel chromatography (60 mg, 85%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6H), 3.17-3.29 (m, 1H), 3.74 (s, 3H), 3.77 (s, 3H), 6.68 (dd, J=8.09, 1.84 Hz, 1H), 6.92-6.98 (m, 1H), 6.99 (d, J=8.82 Hz, 2H), 7.24 (t, J=8.09 Hz, 1H), 7.31-7.50 (m, 5H), 7.68 (d, J=8.09 Hz, 1H), 7.79 (d, J=7.35 Hz, 1H), 7.96 (s, 1H), 8.61 (s, 1H), 8.89 (d, J=8.09 Hz, 1H), 10.18 (s, 1H); MS (APCI) m/z 552 (M+H)+.

Sources & evidence

ORD record
ord-e77e99d5638443be84188b18c6aec2d3
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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