Morpholine → HCID 87315520, compound

HRID 629610Notes

Reaction equation

HRID 629610 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:39]=[C:38]([N:40]4[CH2:45][CH2:44][N:43]([CH2:46][C:47]5[CH2:52][C:51](=O)[CH2:50][CH2:49][C:48]=5[C:54]5[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][CH:55]=5)[CH2:42][CH2:41]4)[CH:37]=[CH:36][C:12]=3[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[C:21]([N+:33]([O-:35])=[O:34])[CH:20]=3)(=[O:18])=[O:17])=[O:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:61]1[CH2:66][CH2:65][O:64][CH2:63][CH2:62]1>ClCCl.CO>[Cl:60][C:57]1[CH:58]=[CH:59][C:54]([C:48]2[CH2:49][CH2:50][CH:51]([N:61]3[CH2:66][CH2:65][O:64][CH2:63][CH2:62]3)[CH2:52][C:47]=2[CH2:46][N:43]2[CH2:42][CH2:41][N:40]([C:38]3[CH:37]=[CH:36][C:12]([C:13]([NH:15][S:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]5[CH2:28][CH2:29][O:30][CH2:31][CH2:32]5)=[C:21]([N+:33]([O-:35])=[O:34])[CH:20]=4)(=[O:18])=[O:17])=[O:14])=[C:11]([O:10][C:6]4[CH:7]=[C:8]5[C:9](=[CH:4][CH:5]=4)[NH:1][CH:2]=[CH:3]5)[CH:39]=3)[CH2:45][CH2:44]2)=[CH:55][CH:56]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 67226633HCID 67226633, compound

Product 1

HCID 87315520HCID 87315520, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of EXAMPLE 249F (120 mg) in dichloromethane (2 mL) and methanol (0.5 mL) was added morpholine (37 mg) and 2-picoline borane complex (15.04 mg). The mixture was stirred overnight. The mixture was then diluted with dichloromethane (200 mL) and washed with aqueous NaHCO3, water, and brine, and dried over Na2SO4. The residue, after evaporation of solvent, was dissolved in dichloromethane and chromatographed with 0-10% 7N NH3 in 5% methanol in dichloromethane to give the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 11.15 (s, 1H), 8.58 (m, 2H), 7.79 (dd, 1H), 7.53 (m, 1H), 7.35 (m, 4H), 7.17 (m, 1H), 7.07 (m, 2H), 6.85 (dd, 1H), 6.64 (dd, 1H), 6.39 (s, 1H), 6.13 (d, 1H), 3.84 (m, 2H), 3.58 (m, 5H), 3.01 (m, 5H), 2.63 (m, 6H), 2.10 (m, 14H), 1.61 (m, 3H), 1.26 (m, 3H).

Workup

  1. washwashed with aqueous NaHCO3, water, and brine
  2. dry with materialdried over Na2SO4
  3. customThe residue, after evaporation of solvent
  4. dissolutionwas dissolved in dichloromethane
  5. customchromatographed with 0-10% 7N NH3 in 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-5e12983b926547c6ac17e55f8b2a59a8
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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