1,2-Dichloroethane → HCID 57382891, compound

HRID 2168241Notes

Reaction equation

HRID 2168241 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][N:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:35][C:36]1[C:44]2[C:43]([N:45]3[CH2:50][CH2:49][CH:48]([NH2:51])[CH2:47][CH2:46]3)=[N:42][CH:41]=[N:40][C:39]=2[NH:38][CH:37]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([NH:51][CH:48]2[CH2:47][CH2:46][N:45]([C:43]3[C:44]4[C:36]([CH3:35])=[CH:37][NH:38][C:39]=4[N:40]=[CH:41][N:42]=3)[CH2:50][CH2:49]2)=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27628212-Methylpyridine-4-carboxylic acidHCID 86710200HCID 86710200, compound

Product 1

HCID 57382891HCID 57382891, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-methyl-4-pyridinecarboxylic acid (41 mg, 0.299 mmol), EDC (86 mg, 0.448 mmol), HOBt (68.6 mg, 0.448 mmol) and DIPEA (0.130 mL, 0.747 mmol) in DCM (1 mL), prestirred for 10 minutes, was added 1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine hydrochloride D11 (80 mg) and the mixture stirred at room temperature for 18 hours. The solvent was removed in vacuo and the mixture purified by MDAP to give the title compound E25 (37 mg), 1H NMR (d6-DMSO) δ 11.52 (1H, s), 8.59 (1H, d), 8.57 (1H, d), 8.22 (1H, s), 7.65 (1H, d), 7.56 (1H, d), 7.07 (1H, s), 4.11-3.99 (3H, m), 3.06 (2H, t), 2.53 (3H, s), 2.37 (3H, s), 1.94 (2H, d), 1.73 (2H, ddd), MS(ES+) 351 [M+H]+.

Workup

  1. stirringthe mixture stirred at room temperature for 18 hours
  2. customThe solvent was removed in vacuo
  3. customthe mixture purified by MDAP

Sources & evidence

ORD record
ord-f062dd03a0c6496c9d139116cae1f0f1
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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