Morpholine → HCID 57635016, compound

HRID 2111326Notes

Reaction equation

HRID 2111326 reaction equation
[CH:1]1([N:7]2[CH2:13][CH2:12][C:11](=[O:14])[NH:10][C:9]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[C:22](OC)[CH:21]=4)=[N:18][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-:51])=N1)C.N1C[CH2:59][O:58]CC1.[CH2:61]([N:63](CC)[CH2:64][CH3:65])[CH3:62]>ClCCl>[CH:1]1([N:7]2[CH2:13][CH2:12][C:11](=[O:14])[NH:10][C:9]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:28]=[CH:27][C:23]([C:24]([N:63]5[CH2:64][CH2:65][O:51][CH2:62][CH2:61]5)=[O:26])=[CH:22][C:21]=4[O:58][CH3:59])=[N:18][C:8]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 68740138HCID 68740138, compoundHCID 178484293HCID 178484293, compound

Product 1

HCID 57635016HCID 57635016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.04 g (0.000095 mole) of 4-(9-cyclohexyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-methoxy-benzoic acid (I-28a), 0.055 g (0.00015 mole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.015 mL (0.00017 mole) of morpholine, 0.04 mL of triethylamine and 2 mL of dichloromethane was stirred overnight at ambient temperature. The mixture was washed with 1 mL of water then with 1.1 mL of 0.34 M sodium hydroxide. The dichloromethane layer was concentrated under reduced pressure, and the residue purified by C18 reverse phase silica gel chromatography, eluting with an acetonitrile-water gradient (10:90-100:0) to give 0.0069 g of 9-cyclohexyl-2-[2-methoxy-4-(morpholine-4-carbonyl)-phenylamino]-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one (I-31)

Workup

  1. washThe mixture was washed with 1 mL of water
  2. concentrationThe dichloromethane layer was concentrated under reduced pressure
  3. customthe residue purified by C18 reverse phase silica gel chromatography
  4. washeluting with an acetonitrile-water gradient (10:90-100:0)

Sources & evidence

ORD record
ord-16bc5a2e8d74452a88ad47d19a19ddee
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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