1,2-Dichloroethane → HCID 178492666, compound

HRID 2168239Notes

Reaction equation

HRID 2168239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][N:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:36][C:37]1[C:45]2[C:44]([N:46]3[CH2:51][CH2:50][CH:49]([NH2:52])[CH2:48][CH2:47]3)=[N:43][CH:42]=[N:41][C:40]=2[NH:39][CH:38]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([NH:52][CH:49]2[CH2:48][CH2:47][N:46]([C:44]3[N:43]=[CH:42][NH:41][C:40]4=[N:39][CH:38]=[C:37]([CH3:36])[C:45]=34)[CH2:51][CH2:50]2)=[O:11])[CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 8199422-Methoxyisonicotinic AcidHCID 86710200HCID 86710200, compound

Product 1

HCID 178492666HCID 178492666, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(methyloxy)-4-pyridinecarboxylic acid (40 mg, 0.261 mmol), EDC (80 mg, 0.418 mmol), HOBt (64.1 mg, 0.418 mmol) and DIPEA (0.114 mL, 0.654 mmol) in DCM (1 mL) was prestirred for 10 minutes before adding 1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine hydrochloride D11 (70 mg) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was then partitioned between DCM (4 mL) and 2M NaOH (4 mL) and the organic phase dried (phase separator) before it was concentrated in vacuo. The crude material was then purified by MDAP. After concentrating the product-containing fractions in vacuo the mixture was triturated with Et2O and filtered to give the title compound E23 as white solid (16 mg), 1H NMR (d6-DMSO) δ 11.54 (1H, s), 8.59 (1H, d), 8.28 (1H, d), 8.22 (1H, s), 7.36 (1H, d), 7.21 (1H, s), 7.07 (1H, s), 4.14-3.99 (3H, m), 3.89 (3H, s), 3.05 (2H, t), 2.36 (3H, s), 1.94 (2H, d), 1.73 (2H, ddd), MS(ES+) 367 [M+H]+.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customThe reaction mixture was then partitioned between DCM (4 mL) and 2M NaOH (4 mL)
  3. customthe organic phase dried (phase separator) before it
  4. concentrationwas concentrated in vacuo
  5. customThe crude material was then purified by MDAP
  6. concentrationAfter concentrating the product-containing fractions in vacuo the mixture
  7. customwas triturated with Et2O
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6f28f2b0d2094a078ebc892fcb5fec1b
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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