Dimethylamine → HCID 86715497, compound

HRID 2284589Notes

Reaction equation

HRID 2284589 reaction equation
O1C[CH2:5][N:4]([CH:7]=[O:8])[CH2:3]C1.CNC.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([C:25]3[CH:26]=[C:27]4[C:31](=[C:32](C(O)=O)[CH:33]=3)[NH:30][N:29]=[CH:28]4)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][C:14]=1[CH3:37].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(#N)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([C:25]3[CH:26]=[C:27]4[C:31](=[C:32]([C:7]([N:4]([CH3:5])[CH3:3])=[O:8])[CH:33]=3)[NH:30][N:29]=[CH:28]4)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][C:14]=1[CH3:37]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8471TriethylamineHCID 20417N-FormylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86715495HCID 86715495, compound

Product 1

HCID 86715497HCID 86715497, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-N,N-dimethyl-1H-indazole-7-carboxamide was prepared analogous to the preparation of 5-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-1H-indazol-7-yl)(morpholino)methanone by the reaction of dimethyl amine (0.55 mL, 1.1 mmol, 2M in THF) with 5-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-1H-indazole-7-carboxylic acid (100 mg, 0.28 mmol), HBTU (140 mg, 0.36 mmol), NEt3 (57 mg, 0.08 mL, 0.57 mmol) in acetonitrile (4 mL). Extractive work-up followed by preparative HPLC purification and neutralization procedure as discussed previously provided desired 5-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-N,N-dimethyl-1H-indazole-7-carboxamide as a white solid. 1H NMR (DMSO-d6): δ 13.05 (s, 1H), 8.63 (dd, 1H, J=1.7 and 4.7 Hz), 8.13 (s, 1H), 7.87 (dd, 1H, J=1.4 and 7.6 Hz), 7.81 (s, 1H), 7.46 (dd, 1H, J=4.7 and 7.6 Hz), 7.32 (d, 1H, J=7.3 Hz), 7.02-6.98 (m, 1H), 6.95-6.89 (app m. 2H), 2.93 (br s, 3H), 2.57 (br s, 3H), 2.09 (s, 3H).19F NMR (DMSO-d6): δ −118.91. LCMS: rt 4.63 min (A), purity 97%, MS (m/e) 375 (MH+).

Workup

  1. customExtractive work-up followed by preparative HPLC purification and neutralization procedure

Sources & evidence

ORD record
ord-bcb17ac78a6e4441b382b48c86459d5c
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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