Diisopropylethylamine → HCID 67344825, compound

HRID 1257607Notes

Reaction equation

HRID 1257607 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][CH2:12][C:13](Cl)=[O:14].[C:16]1([S:22]([N:25]2[C:29]3=[N:30][CH:31]=[C:32]([NH:41][C:42](=[O:50])[CH2:43][C:44]4[C:45]([CH3:49])=[N:46][O:47][CH:48]=4)[C:33]([NH:34][CH:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)=[C:28]3[CH:27]=[CH:26]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[C:16]1([S:22]([N:25]2[C:29]3=[N:30][CH:31]=[C:32]([NH:41][C:42](=[O:50])[CH2:43][C:44]4[C:45]([CH3:49])=[N:46][O:47][CH:48]=4)[C:33]([NH:34][CH:35]4[CH2:40][CH2:39][N:38]([C:13](=[O:14])[CH2:12][O:11][CH3:10])[CH2:37][CH2:36]4)=[C:28]3[CH:27]=[CH:26]2)(=[O:23])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 67379119HCID 67379119, compound

Product 1

HCID 67344825HCID 67344825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Diisopropylethylamine (0.107 ml, 0.615 mmol) and methoxyacetyl chloride (0.028 ml, 0.308 mmol) were added sequentially to a solution of N-[1-benzenesulfonyl-4-(piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(3-methyl-isoxazol-4-yl)-acetamide (hydrochloride salt) (0.205 mmol) in CH2Cl2 (2 ml) at 25° C. The reaction mixture was stirred for 3 h at 25° C., then was partitioned between saturated NaHCO3 (6 ml) and CH2Cl2 (2 ml). The phases were separated using a phase separation column (Biotage) and the organic layer was concentrated under reduced pressure to give crude N-{1-benzenesulfonyl-4-[1-(2-methoxy-acetyl)-piperidin-4-ylamino]-1H-pyrrolo[2,3-b]pyridin-5-yl}-2-(3-methyl-isoxazol-4-yl)-acetamide as a brown oil/solid. LCMS (Method G, ESI): RT=0.73 min, m+H=567.3. This material was used in the next step below without additional purification or characterization.

Workup

  1. customwas partitioned between saturated NaHCO3 (6 ml) and CH2Cl2 (2 ml)
  2. customThe phases were separated
  3. customa phase separation column (Biotage)
  4. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e7ae515e2e1a4899b037c9092572494d
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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