Morpholine → HCID 59580031, compound

HRID 2279618Notes

Reaction equation

HRID 2279618 reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:28]12([CH2:38][NH:39][C:40]([C:42]3[C:43]([CH3:57])=[N:44][N:45]([C:47]4[N:52]=[C:51]([C:53](O)=[O:54])[C:50]([CH3:56])=[CH:49][N:48]=4)[CH:46]=3)=[O:41])[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2.[NH:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:28]12([CH2:38][NH:39][C:40]([C:42]3[C:43]([CH3:57])=[N:44][N:45]([C:47]4[N:52]=[C:51]([C:53]([N:58]5[CH2:63][CH2:62][O:61][CH2:60][CH2:59]5)=[O:54])[C:50]([CH3:56])=[CH:49][N:48]=4)[CH:46]=3)=[O:41])[CH2:29][CH:30]3[CH2:31][CH:32]([CH2:33][CH:34]([CH2:36]3)[CH2:35]1)[CH2:37]2

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59579898HCID 59579898, compound

Product 1

HCID 59580031HCID 59580031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BOP (88 mg, 8 mmol) is added to a solution of 2-{4-[(adamantan-1-ylmethyl)-carbamoyl]-3-methyl-pyrazol-1-yl}-5-methyl-pyrimidine-4-carboxylic acid (41 mg, 0.1 mmol), morpholine (13 mg, 0.15 mmol) and DIEA (39 mg, 0.3 mmol) in DCM (3 mL). The solution is stirred overnight, evaporated and partitioned between EtOAc and saturated aqueous sodium bicarbonate. The organic layer is washed with brine, dried and evaporated. Purification by PTLC, eluting with a mixture of 5% MeOH and 1% TEA in DCM, affords the title compound. 1H NMR (CDCl3): 8.80 (s, 1H), 8.65 (s, 1H), 5.93 (s, 1H), 3.81 (s, 4H), 3.63-3.66 (m, 1H), 3.46 (s, 1H), 3.29 (t, 1H), 3.10-3.15 (m, 2H), 2.85-2.90 (m, 1H), 2.58 (s, 3H), 2.31 (s, 3H), 1.99 (s, 3H), 1.53-1.73 (m, 12H). MS (M+1)=479.37; RT=1.30 min. *IC50.

Workup

  1. customevaporated
  2. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  3. washThe organic layer is washed with brine
  4. customdried
  5. customevaporated
  6. customPurification by PTLC
  7. washeluting with a mixture of 5% MeOH and 1% TEA in DCM

Sources & evidence

ORD record
ord-40c0ebc161ad4091855af451aed3a51d
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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