Morpholine → HCID 15949064, compound

HRID 225988Notes

Reaction equation

HRID 225988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH2:24][CH2:25][NH:26][S:27]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH:37]=O)(=[O:29])=[O:28])=[C:5]2[CH2:39][CH2:40][CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48]C)=[O:47])=[CH:44][CH:43]=1.[NH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([CH2:24][CH2:25][NH:26][S:27]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37][N:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1)(=[O:29])=[O:28])=[C:5]2[CH2:39][CH2:40][CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([OH:48])=[O:47])=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 25223196HCID 25223196, compound

Product 1

HCID 15949064HCID 15949064, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To methyl 4-{3-[5-chloro-1-(diphenylmethyl)-2-(2-{[(2-formylbenzyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]propyl}benzoate (Example 16, Step 5, 58 mg, 0.081 mmol) in DCE (2 mL) at 0° C. were added morpholine (0.0092 mL, 0.105 mmol) and NaBH(OAc)3 (27 mg, 0.13 mmol) and the reaction mixture was allowed to warm to rt overnight. The reaction was quenched with sat. NaHCO3, extracted with EtOAc, and dried over MgSO4. Purification by silica gel chromatography (35% to 50% EtOAc/hexanes) gave the desired product as a white solid (41 mg, 64%).

Workup

  1. customThe reaction was quenched with sat. NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customPurification by silica gel chromatography (35% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-40a1a4e6043b4087b6e67c2e2ed0c562
Source dataset
uspto-grants-2009_07
Patent number
US07557135B2

Reaction notes

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