Methylamine → HCID 57441915, compound

HRID 2088483Notes

Reaction equation

HRID 2088483 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[C:10]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])[C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[C:20]([O:27][CH3:28])[CH:19]=3)=[N:14][C:12]=2[N:13]=1.[CH3:36][N:37](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.C(N(CC)CC)C>C1COCC1>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[C:10]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])[C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH:37][CH3:36])=[O:23])=[C:20]([O:27][CH3:28])[CH:19]=3)=[N:14][C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59703410HCID 59703410, compound

Product 1

HCID 57441915HCID 57441915, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-[2,4-Bis-((S)-3-methyl-morpholin-4-yl)-pyrido[2,3-d]pyrimidin-7-yl]-2-methoxy-benzoic acid (1 equiv) was dissolved in THF (0.1 M) and HBTU (1.5 equiv) was added. Methylamine in THF (15 equiv) was added dropwise followed by triethylamine (1.5 equiv) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between water and CH2Cl2. The aqueous phase was extracted with CH2Cl2. Combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by preparative HPLC to give the desired product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was partitioned between water and CH2Cl2
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. dry with materialCombined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6bd00ff054484da0a578186406f59a01
Source dataset
uspto-grants-2013_05
Patent number
US08435985B2

Reaction notes

Loading…