Dichloromethane → HCID 68517261, compound

HRID 1948334Notes

Reaction equation

HRID 1948334 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Cl:6][C:7]1[C:11]([Cl:12])=[C:10]([CH3:13])[NH:9][C:8]=1[C:14]([NH:16][C@@H:17]1[CH2:22][CH2:21][N:20]([C:23]2[S:24][C:25]([C:35]([OH:37])=[O:36])=[C:26]([C:28]([NH:30][CH2:31][CH2:32][O:33][CH3:34])=[O:29])[N:27]=2)[CH2:19][C@@H:18]1[O:38][CH3:39])=[O:15].C(Cl)Cl>CO>[Cl:6][C:7]1[C:11]([Cl:12])=[C:10]([CH3:13])[NH:9][C:8]=1[C:14]([NH:16][C@@H:17]1[CH2:22][CH2:21][N:20]([C:23]2[S:24][C:25]([C:35]([O-:37])=[O:36])=[C:26]([C:28]([NH:30][CH2:31][CH2:32][O:33][CH3:34])=[O:29])[N:27]=2)[CH2:19][C@@H:18]1[O:38][CH3:39])=[O:15].[CH2:1]([NH2+:3][CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 11995989HCID 11995989, compound

Product 1

HCID 68517261HCID 68517261, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diethylamine (0.0058 mL, 0.056 mmol, Aldrich) was added to a suspension of 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-{[(2-methoxyethyl)amino]carbonyl}-1,3-thiazole-5-carboxylic acid (0.03 g, 0.056 mmol, Example 387) in methanol (5 mL). After stirring five minutes, methylene chloride was added until solution was homogeneous. The reaction was concentrated and the resulting solid was dried overnight (0.024 g). MS (ES) MH+: 534 for C24H37Cl2N6O6S; NMR: 1.16 (t, 3 H) 1.74 (s, 2 H) 2.19 (s, 3 H) 2.91 (q, 3 H) 3.25 (s, 3 H) 3.32 (s, 4 H) 3.37 (s, 3 H) 3.42 (d, 2 H) 3.53 (s, 1 H) 3.94 (s, 1 H) 4.22 (s, 2 H) 7.17 (d, 1 H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe resulting solid was dried overnight (0.024 g)

Sources & evidence

ORD record
ord-8c7011f0ecd14042856610357db729e6
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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