Dimethylformamide → HCID 57410846, compound

HRID 1502269Notes

Reaction equation

HRID 1502269 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:27])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:19]([CH:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[O:20])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1.CN(C)C=O.[CH:33](N(CC)C(C)C)(C)[CH3:34].ICC>>[CH2:33]([N:24]1[CH2:25][CH2:26][CH:21]([C:19]([NH:18][C:13]2[N:14]=[CH:15][C:16]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[CH3:27])[CH:17]=3)=[O:20])[CH2:22][CH2:23]1)[CH3:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6340Iodoethane2×HCID 81531Diisopropylethylamine2×HCID 71115080HCID 71115080, compound

Product 1

HCID 57410846HCID 57410846, compoundYield 41.4%

Procedure

To a solution of N-(7-(5-fluoro-2-methylphenyl)isoquinolin-3-yl)piperidine-4-carboxamide (110.6 mg, 0.1936 mmol) in N,N-dimethylformamide (2.0 mL, 26 mmol) was added N,N-diisopropylethylamine (0.1 mL, 0.574 mmol) and iodoethane (19.0 uL, 0.238 mmol). The reaction was stirred at room temperature for 19 hours, and then N,N-diisopropylethylamine (0.1 mL) and iodoethane (30 uL, 0.375 mmol) were added. After an additional 4 hours, the mixture was evaporated in vacuo. The crude product was purified via reverse phase HPLC and lyophilized to yield 31.4 mg (41%) of 1-ethyl-N-(7-(5-fluoro-2-methylphenyl)isoquinolin-3-yl)piperidine-4-carboxamide. LCMS (ESI): RT (Min)=4.370, M+H=392.1, method=E; 1H NMR (400 MHz, DMSO-d6) δ 10.76 (s, 1H), 9.19 (s, 1H), 8.53 (s, 1H), 8.06 (s, 1H), 7.96 (d, J=8.6 Hz, 1H), 7.73 (d, J=8.5 Hz, 1H), 7.39 (s, 1H), 7.18 (d, J=8.9 Hz, 2H), 3.53 (unresolved, 2H), 3.08 (unresolved, 2H), 2.83 (unresolved, 3H), 2.25 (s, 3H), 2.07 (unresolved, 2H), 1.90 (unresolved, 2H), 1.22 (unresolved, 3H).

Workup

  1. waitAfter an additional 4 hours
  2. customthe mixture was evaporated in vacuo
  3. customThe crude product was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-5301f9e1b4f74f8c824c59efd512bcc2
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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