1,2-Dichloroethane → HCID 178430155, compound

HRID 2168237Notes

Reaction equation

HRID 2168237 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:34][C:35]1[C:43]2[C:42]([N:44]3[CH2:49][CH2:48][CH:47]([NH2:50])[CH2:46][CH2:45]3)=[N:41][CH:40]=[N:39][C:38]=2[NH:37][CH:36]=1>C(Cl)Cl>[CH3:34][C:35]1[C:43]2[C:38]([NH:39][CH:40]=[N:41][C:42]=2[N:44]2[CH2:49][CH2:48][CH:47]([NH:50][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[O:9])[CH2:46][CH2:45]2)=[N:37][CH:36]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 1018Picolinic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86710200HCID 86710200, compound

Product 1

HCID 178430155HCID 178430155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-pyridine carboxylic acid (41.4 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 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 E21 (34 mg), 1H NMR (d6-DMSO) δ 11.52 (1H, s), 8.69 (1H, d), 8.65 (1H, d), 8.21 (1H, s), 8.06 (1H, d), 8.00 (1H, t), 7.61 (1H, t), 7.06 (1H, s), 4.08 (1H, m), 4.00 (2H, d), 3.05 (2H, t), 2.37 (3H, s), 2.0-1.7 (4H, m), MS(ES+) 337 [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 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-containing fractions
  7. customto afford E21 (34 mg), 1H NMR (d6-DMSO) δ 11.52 (1H, s), 8.69 (1H, d), 8.65 (1H, d), 8.21 (1H, s), 8.06 (1H, d), 8.00 (1H, t), 7.61 (1H, t), 7.06 (1H, s), 4.08 (1H, m), 4.00 (2H, d), 3.05 (2H, t), 2.37 (3H, s), 2.0-1.7 (4H, m), MS(ES+) 337 [M+H]+

Sources & evidence

ORD record
ord-472b77cc221040e391a4dd7d0b336bfd
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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