1-Methylpiperazine → HCID 66604454, compound

HRID 2410899Notes

Reaction equation

HRID 2410899 reaction equation
[C:1]([C:4]1[C:9]2[NH:10][C:11]3[CH:12]=[C:13]([C:17](O)=[O:18])[CH:14]=[CH:15][C:16]=3[C:8]=2[N:7]=[C:6]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=2)[CH:5]=1)(=[O:3])[NH2:2].[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:27][C:22]1[CH:21]=[C:20]([C:6]2[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:9]3[NH:10][C:11]4[CH:12]=[C:13]([C:17]([N:32]5[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]5)=[O:18])[CH:14]=[CH:15][C:16]=4[C:8]=3[N:7]=2)[CH:25]=[CH:24][C:23]=1[F:26]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66604725HCID 66604725, compound

Product 1

HCID 66604454HCID 66604454, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-carbamoyl-2-(3-chloro-4-fluorophenyl)-5H-pyrido[3,2-b]indole-7-carboxylic acid 431D (55 mg, 0.143 mmol), 1-methylpiperazine (0.032 mL, 0.287 mmol), N,N-diisopropylethylamine (0.075 mL, 0.430 mmol) and HATU (109 mg, 0.287 mmol) in DMF (1 mL) was stirred for overnight. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 466.16 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.82 (s, 1H), 8.62 (s, 1H), 8.53 (s, 1H), 8.50 (dd, 1H, J=7.1, 2.1), 8.34 (m, 2H), 7.99 (s, 1H), 7.79 (s, 1H), 7.62 (t, 1H, J=8.8), 7.28(d, 1H, J=8.0), 3.67 (bs, 4H), 2.37 (bs, 4H), 2.22 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified

Sources & evidence

ORD record
ord-294998bb8a114e89bfdc4e4022636b4f
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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