Diethylamine → HCID 178464014, compound

HRID 1888263Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:30]([NH2:32])=[O:31])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=4)[CH:21]=3)[NH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6].C([O-])([O-])=O.[K+].[K+].[CH2:39]([NH:41][CH2:42][CH3:43])[CH3:40]>CN(C=O)C>[CH2:39]([N:41]([CH2:42][CH3:43])[CH2:2][CH2:3][CH2:4][S:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[C:18]([C:30]([NH2:32])=[O:31])[CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=4)[CH:21]=3)[NH:16][N:15]=2)[CH2:10][CH2:9]1)(=[O:7])=[O:6])[CH3:40]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-5-(3-fluorophenyl)-1H-indazole-7-carboxamide (0.222 mmol) in DMF (4 mL) was added K2CO3 (61 mg, 0.444 mmol) and diethyl amine (115 uL, 1.11 mmol). The reaction mixture was heated to 100° C. overnight. The solution was filtered and the filtrate was purified by using a Gilson semi-preparative HPLC system with a YMC ODS-A (C-18) column 50 mm by 20 mm ID, eluting with 10% B to 80% B in 10 min, hold for 1 min where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to afford the title compound (24.7 mg, 22% for 2 steps).

Workup

filtrationThe solution was filtered
customthe filtrate was purified
washeluting with 10% B to 80% B in 10 min

Sources & evidence

ORD record: ord-07e1e338beeb43829f962ab91ac6cebe
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501780B2

Reaction notes

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