Lithium borohydride → N-[1-(Hydroxymethyl)isoquinolin-5-yl]-N'-[4-(trifluoromethyl)benzyl]urea

HRID 1181497Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]([NH:15][C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[O:17])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=O.[BH4-].[Li+]>C1COCC1.C1(C)C=CC=CC=1>[OH:2][CH2:3][C:5]1[C:14]2[C:9](=[C:10]([NH:15][C:16]([NH:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=3)=[O:17])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

N-[1-(Methoxycarbonyl)isoquinolin-5-yl]-N′-[4-(trifiluoromethyl)benzyl]urea (Example 116, 70 mg, 0.174 mmol) was suspended in a mixture of THF (5 ml) and toluene (5 ml). Lithium borohydride (50 mg, 2.27 mmol) was added and the reaction mixture heated at 60° C. for 1 hour. The reaction was cooled to room temperature and allowed to stand for 1 week. The crystalline product was collected by filtration, washed with toluene (2 ml), then triturated with 1:1 TBF-dichloromethane (2 ml), triturated again with THF (2 ml) and dried under vacuum to give the title compound (8 mg, 12%). m/z (ES+) 376 (M+H)+.

Workup

temperatureThe reaction was cooled to room temperature
waitto stand for 1 week
filtrationThe crystalline product was collected by filtration
washwashed with toluene (2 ml)
customtriturated with 1:1 TBF-dichloromethane (2 ml)
customtriturated again with THF (2 ml)
customdried under vacuum

Sources & evidence

ORD record: ord-2608f4311c004dffb8a6f95bc7793811
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285563B2

Reaction notes

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