6-Chloro-1-benzothiophene-2-carboxylic acid → HCID 53907772, compound

HRID 1433007Notes

Reaction equation

HRID 1433007 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([OH:12])=O)[S:7][C:6]=2[CH:13]=1.C(OC([N:21]1[C:29]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[CH:23]=[C:22]1[CH2:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][C:32]1=[O:37])=O)(C)(C)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([N:34]3[CH2:35][CH2:36][N:31]([CH2:30][C:22]4[NH:21][C:29]5[CH:28]=[CH:27][N:26]=[CH:25][C:24]=5[CH:23]=4)[C:32](=[O:37])[CH2:33]3)=[O:12])[S:7][C:6]=2[CH:13]=1

Participants

3

Reactant 2

HCID 71419196-Chloro-1-benzothiophene-2-carboxylic acidHCID 544278362-(2-Oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 53907772HCID 53907772, compound

Procedure

The title compound is prepared as described in EXAMPLE 123 using 6-chloro-benzo[b]thiophene-2-carboxylic acid, EXAMPLE 1 and 2-(2-oxopiperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridin-1-carboxylic acid tert-butyl ester EXAMPLE 69. The mixture is stirred overnight, then concentrated to dryness. The residue is diluted with CH2Cl2 and washed with saturated sodium bicarbonate and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a solid. The crude material can be used in the subsequent step without further purification.

Workup

  1. customThe title compound is prepared
  2. concentrationconcentrated to dryness
  3. additionThe residue is diluted with CH2Cl2
  4. washwashed with saturated sodium bicarbonate and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c5dfb32fc2b45c6b5055ee1b0155a4d
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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