1-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone dihydrochloride → AT-Iap

HRID 1475529Notes

Reaction equation

HRID 1475529 reaction equation
Cl.Cl.[F:3][C:4]1[CH:39]=[CH:38][C:7]([CH2:8][C:9]2[CH:10]=[C:11]3[N:17]([C:18](=[O:35])[CH2:19][N:20]4[CH2:25][C@@H:24]([CH3:26])[NH:23][CH2:22][C@@H:21]4[CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][C@H:29]4[CH3:34])[CH2:16][C:15]([CH3:37])([CH3:36])[C:12]3=[N:13][CH:14]=2)=[CH:6][CH:5]=1>O>[F:3][C:4]1[CH:39]=[CH:38][C:7]([CH2:8][C:9]2[CH:10]=[C:11]3[N:17]([C:18](=[O:35])[CH2:19][N:20]4[CH2:25][C@@H:24]([CH3:26])[NH:23][CH2:22][C@@H:21]4[CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][C@H:29]4[CH3:34])[CH2:16][C:15]([CH3:37])([CH3:36])[C:12]3=[N:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 714716131-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone dihydrochloride

Product 1

HCID 70980530AT-IapYield 109.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-ylmethyl)-piperazin-1-yl]-ethanone dihydrochloride (1.8 g) was dissolved in water (50 mL) and the resulting solution extracted with ethyl acetate (50 mL). The aqueous phase was basified (pH 8) with saturated aqueous NaHCO3 then was extracted with DCM (5×50 mL). The combined DCM extracts were dried (Na2SO4) and evaporated in vacuo to give the title compound (1.72 g) as a foam. 1H NMR (Me-d3-OD): 8.24 (1H, s), 8.07 (1H, d), 7.24 (2H, dd), 7.03 (2H, t), 4.19-4.06 (1H, m), 3.99 (3H, d), 3.90 (1H, d), 3.71 (1H, d), 3.65-3.48 (2H, m), 3.19-2.70 (8H, m), 2.60-2.40 (2H, m), 2.26 (1H, s), 2.09-1.93 (1H, m), 1.87 (1H, d), 1.41 (6H, d), 1.04 (3H, d), 0.97 (3H, d).

Workup

  1. extractionthe resulting solution extracted with ethyl acetate (50 mL)
  2. extractionthen was extracted with DCM (5×50 mL)
  3. dry with materialThe combined DCM extracts were dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ac26ab26d0c442e7a458146e1686ff50
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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