Morpholine → HCID 70225157, compound

HRID 1531559Notes

Reaction equation

HRID 1531559 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:34][CH2:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([NH:44][S:45]([CH3:48])(=[O:47])=[O:46])=[CH:40][CH:39]=1)[CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([OH:25])=O)[CH:21]=2)[NH:16][C:15]=1[C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH:89]1[CH2:94][CH2:93][O:92][CH2:91][CH2:90]1>C(Cl)Cl.CO.C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([N:89]3[CH2:94][CH2:93][O:92][CH2:91][CH2:90]3)=[O:25])[CH:21]=2)[NH:16][C:15]=1[C:26]1[CH:27]=[C:28]([CH3:33])[CH:29]=[C:30]([CH3:32])[CH:31]=1)[CH2:34][CH2:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([NH:44][S:45]([CH3:48])(=[O:46])=[O:47])=[CH:40][CH:39]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 2724699PyBOPHCID 21254046HCID 21254046, compound

Product 1

HCID 70225157HCID 70225157, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 33.4 mg (0.050 mmol) of [3-[2-[benzyloxycarbonyl-[4-[4-(methanesulfonylamino)phenyl]butyl]amino]-ethyl]-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid, 26.0 mg (0.050 mmol) of PyBOP reagent, 0.010 mL (7.3 mg, 0.072 mmol) of triethylamine, 0.0065 mL (6.5 mg, 0.075 mmol) of morpholine, and 0.0400 mL of dry methylene chloride was stirred under nitrogen at room temperature in a stoppered flask. After 5.5 hours, the solution was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the crude product by preparative tlc on 2 1000-micron silica gel GF plates (developed in 93:7 CH2Cl2) afforded a quantitative yield amorphous, white solid; homogeneous by TLC in 95:5 CH2Cl2-MeOH. 500 MHz 1H NMR (CDCl3) was complex, owing to rotamers, but was consistent with the assigned structure. Mass spectrum (ESI): m/e=737.2 (M+H).

Workup

  1. customthe solution was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude product by preparative tlc on 2 1000-micron silica gel GF plates (developed in 93:7 CH2Cl2)
  6. customafforded a quantitative yield amorphous

Sources & evidence

ORD record
ord-462113f8ff6e4a1f903b5ac42ed37d99
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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