2-Methylbenzoyl chloride → HCID 57382892, compound

HRID 2168242Notes

Reaction equation

HRID 2168242 reaction equation
Cl.[CH3:2][C:3]1[C:11]2[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]3)=[N:9][CH:8]=[N:7][C:6]=2[NH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH3:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>C(Cl)Cl>[CH3:28][C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([NH:18][CH:15]1[CH2:16][CH2:17][N:12]([C:10]2[C:11]3[C:3]([CH3:2])=[CH:4][NH:5][C:6]=3[N:7]=[CH:8][N:9]=2)[CH2:13][CH2:14]1)=[O:32]

Participants

5

Reactant 3

HCID 702762-Methylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 86710200HCID 86710200, compound

Product 1

HCID 57382892HCID 57382892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine hydrochloride D11 (70 mg) and DIPEA (0.11 mL, 0.605 mmol) in DCM (1 mL) was added 2-methylbenzoyl chloride (70.2 mg, 0.454 mmol) and the reaction stirred at room temperature for 18 hours. The solvent was removed in vacuo and the mixture purified by MDAP to give the title compound E26 (25 mg) as a pale pink solid, 1H NMR (d6-DMSO) 11.55 (1H, brs), 8.26 (1H, d), 8.21 (1H, s), 7.30 (2H, m), 7.25 (2H, m), 7.06 (1H, s), 4.0 (3H, m), 3.06 (2H, t), 2.35 (3H, s), 2.35 (3H, s), 1.94 (2H, m), 1.67 (2H, m), MS(ES+) 350 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe mixture purified by MDAP

Sources & evidence

ORD record
ord-713b8a26eb6d4186b4006350344c13ba
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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