Triethylamine → N-(3-tert-butylphenyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-phenylpiperidine-4-carboxamide

HRID 216028Notes

Reaction equation

HRID 216028 reaction equation
[CH3:1][C:2]1[C:10]2[CH:9]([N:11]3[CH2:16][CH2:15][C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)([C:17](O)=[O:18])[CH2:13][CH2:12]3)[NH:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[C:26]([C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33])([CH3:29])([CH3:28])[CH3:27].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[C:26]([C:30]1[CH:31]=[C:32]([NH:33][C:17]([C:14]2([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:13][CH2:12][N:11]([C:9]3[C:10]4[C:2]([CH3:1])=[CH:3][NH:4][C:5]=4[N:6]=[CH:7][N:8]=3)[CH2:16][CH2:15]2)=[O:18])[CH:34]=[CH:35][CH:36]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 793343-tert-ButylanilineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178430809HCID 178430809, compound

Product 1

HCID 44482389N-(3-tert-butylphenyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-phenylpiperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-phenylpiperidine-4-carboxylic acid from step B (33 mg, 0.1 mmol) in DMF (2 mL) was added 3-tert-butylaniline (15 mg, 1.0 mmol), BOP (50 mg, 0.11 mmol) and triethylamine (0.04 mL, 0.3 mmol). The reaction mixture was stirred at room temperature for 20 hours, and the amide product was isolated by prep HPLC to give the title compound.

Sources & evidence

ORD record
ord-9797646186d9420f9123c2d08397bc07
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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