3-Methoxyphenyl isocyanate → HCID 178491217, compound

HRID 1068940Notes

Reaction equation

O.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[N:17][C:18]=3[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[NH:13][N:12]=2)=[CH:6][CH:5]=1.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([N:36]=[C:37]=[O:38])[CH:33]=[CH:34][CH:35]=1>C1COCC1>[Cl:27][C:23]1[CH:22]=[C:21]([NH:20][C:18]2[N:17]=[CH:16][N:15]=[C:14]3[NH:13][N:12]=[C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([CH2:3][NH:2][C:37]([NH:36][C:32]5[CH:33]=[CH:34][CH:35]=[C:30]([O:29][CH3:28])[CH:31]=5)=[O:38])=[CH:5][CH:6]=4)[C:19]=23)[CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 115 mg (0.3 mmol) of 3-(4-aminomethyl-phenylamino)-4-(3chloro-phenylamino)-1H-pyrazolo-[3,4-d]pyrimidine hydrate (see Step 77.5), 0.041 ml (0.318 mmol) of 3-methoxy-phenyl isocyanate and 4 ml of THF is stirred at 20° C. for 15 hours and then concentrated by evaporation in vacuo. After recrystallization of the residue from ethyl acetate/hexane, 4-(3-chloro-phenylamino)-3-{4-[(3-methoxy-phenyl-amino)-carbonylamino-methyl]-phenylamino}-1H-pyrazolo-[3,4-d]pyrimidine is obtained in the form of the monohydrate; m.p. 157-160° C.; ESI-MS: (M−H)−=513.

Workup

concentrationconcentrated by evaporation in vacuo
customAfter recrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record: ord-ef0d52286a264cd09d6047698b258702
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251911B1

Reaction notes

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