1,2-Dichloroethane → HCID 178425842, compound

HRID 2168238Notes

Reaction equation

HRID 2168238 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH: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[N:7]=[CH:6][C:5]([C:8]([NH:51][CH:48]2[CH2:47][CH2:46][N:45]([C:43]3[N:42]=[CH:41][NH:40][C:39]4=[N:38][CH:37]=[C:36]([CH3:35])[C:44]=34)[CH2:50][CH2:49]2)=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 86710200HCID 86710200, compound

Product 1

HCID 178425842HCID 178425842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-methyl-3-pyridinecarboxylic acid (46.1 mg, 0.336 mmol), EDC (68.7 mg, 0.359 mmol), HOBt (54.9 mg, 0.359 mmol) and DIPEA (0.098 mL, 0.560 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 (60 mg) and the mixture stirred for 18 hours. The mixture was partitioned between DCM (4 mL) and aqueous sodium bicarbonate (4 mL) and the aqueous phase was extracted with further DCM (4 mL). The combined organic fractions were concentrated in vacuo and purified by MDAP. The solvent was then removed in vacuo from the product containing fractions, to afford E22 (14 mg), 1H NMR (d6-DMSO) δ 11.53 (1H, s), 8.90 (1H, s), 8.47 (1H, d), 8.22 (1H, s), 8.10 (1H, d), 7.35 (1H, d), 7.07 (1H, s), 4.08 (1H, m), 4.02 (2H, d), 3.95 (2H, t), 2.47 (3H, s), 2.37 (3H, s), 1.95 (2H, d), 1.73 (2H, ddd), MS(ES+) 351 [M+H]+.

Workup

  1. stirringthe mixture stirred for 18 hours
  2. customThe mixture was partitioned between DCM (4 mL) and aqueous sodium bicarbonate (4 mL)
  3. extractionthe aqueous phase was extracted with further DCM (4 mL)
  4. concentrationThe combined organic fractions were concentrated in vacuo
  5. custompurified by MDAP
  6. customThe solvent was then removed in vacuo from the product
  7. additioncontaining fractions
  8. customto afford E22 (14 mg), 1H NMR (d6-DMSO) δ 11.53 (1H, s), 8.90 (1H, s), 8.47 (1H, d), 8.22 (1H, s), 8.10 (1H, d), 7.35 (1H, d), 7.07 (1H, s), 4.08 (1H, m), 4.02 (2H, d), 3.95 (2H, t), 2.47 (3H, s), 2.37 (3H, s), 1.95 (2H, d), 1.73 (2H, ddd), MS(ES+) 351 [M+H]+

Sources & evidence

ORD record
ord-183b432fdef04b86bdc7d00a26f915d4
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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