Hydrogen Bromide → HCID 56959785, compound

HRID 1038859Notes

Reaction equation

C(OC([NH:11][CH2:12][C:13]1([CH3:45])[CH2:18][CH2:17][N:16]([C:19]2[C:20]3[O:44][CH:43]=[CH:42][C:21]=3[N:22]=[C:23]([NH:25][C:26]3[CH:34]=[C:33]4[C:29]([CH:30]=[N:31][N:32]4C(OC(C)(C)C)=O)=[CH:28][CH:27]=3)[N:24]=2)[CH2:15][CH2:14]1)=O)C1C=CC=CC=1.ClC1N=C(Cl)C2OC=CC=2N=1.CC1(CNC(=O)OCC2C=CC=CC=2)CCNCC1.NC1C=C2C(C=NN2C(OC(C)(C)C)=O)=CC=1.Br>CC(O)=O.O>[NH2:11][CH2:12][C:13]1([CH3:45])[CH2:18][CH2:17][N:16]([C:19]2[C:20]3[O:44][CH:43]=[CH:42][C:21]=3[N:22]=[C:23]([NH:25][C:26]3[CH:34]=[C:33]4[C:29]([CH:30]=[N:31][NH:32]4)=[CH:28][CH:27]=3)[N:24]=2)[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of tert-butyl 6-(4-(4-((benzyloxycarbonylamino)methyl)-4-methylpiperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-1H-indazole-1-carboxylate (0.13 g, 0.213 mmol, (prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] with benzyl (4-methylpiperidin-4-yl)methylcarbamate [U.S. Pat. No. 6,140,333 example 3 step 5]), B with tert-butyl 6-amino-1H-indazole-1-carboxylate [Frontier] and C) in AcOH (3 mL) was added HBr (1 mL). The mixture was stirred at about 40° C. for about 8 h. Water (30 mL) was added and the mixture was extracted with DCM (4×20 mL). The mixture was concentrated in vacuo to give 4-(4-(aminomethyl)-4-methylpiperidin-1-yl)-N-(1H-indazol-6-yl)furo[3,2-d]pyrimidin-2-amine (0.015 g, 19%): LC/MS (Table 2, Method h) Rt=1.72 min; MS m/z: 378 (M+H)+. Syk IC50=A

Workup

custom(prepared
extractionthe mixture was extracted with DCM (4×20 mL)
concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-7377d8edb9ba4167ba091024fdb63831
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551981B2

Reaction notes

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