Methanesulfonamide → HCID 86689701, compound

HRID 1775859Notes

Reaction equation

HRID 1775859 reaction equation
[C:1]([C:5]1[CH:48]=[CH:47][C:8]([C:9]([NH:11][C@@H:12]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:35][CH:34]=4)=[CH:29][N:28]=3)=[CH:23][CH:22]=2)[C:13]([NH:15][CH2:16][C:17](O)=[O:18])=[O:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:49][S:50]([NH2:53])(=[O:52])=[O:51].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C@@H:12]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:32]=[CH:31][C:30]([C:33]4[CH:34]=[CH:35][C:36]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:37][CH:38]=4)=[CH:29][N:28]=3)=[CH:23][CH:22]=2)[C:13]([NH:15][CH2:16][C:17]([NH:53][S:50]([CH3:49])(=[O:52])=[O:51])=[O:18])=[O:14])=[O:10])=[CH:47][CH:48]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86582689HCID 86582689, compound

Product 1

HCID 86689701HCID 86689701, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

TEA (32.1 μl, 0.23 mmol) was added to a suspension of (S)-(2-(4-(tert-butyl)benzamido)-3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)propanoyl)glycine Compound 297 (75.0 mg, 0.11 mmol), methanesulfonamide (12.1 mg, 0.13 mmol), HATU (52.6 mg, 0.14 mmol) and DMAP (1.41 mg, 0.01 mmol) in DCM (2 mL). The resultant yellow suspension was stirred at room temperature for 3 h. The reaction mixture was washed with saturated aqueous NaHCO3 (2 mL) and the mixture passed through a phase separation cartridge. The organic phase was concentrated in vacuo to afford a yellow solid. The crude product was purified by chromatography (EA/1% AcOH in hexanes) to afford 9 mg (11%) (S)-4-(tert-butyl)-N-(3-(4-(5-(4-(heptyloxy)phenyl)pyrimidin-2-yl)phenyl)-1-((2-(methylsulfonamido)-2-oxoethyl)amino)-1-oxopropan-2-yl)benzamide, Compound 381 as a yellow solid. LCMS-ESI (m/z) calculated for C40H49N5O6S: 727.3. found 728.0 [M+H]+, tR=10.51 min (Method 10).

Workup

  1. washThe reaction mixture was washed with saturated aqueous NaHCO3 (2 mL)
  2. customthe mixture passed through a phase separation cartridge
  3. concentrationThe organic phase was concentrated in vacuo
  4. customto afford a yellow solid
  5. customThe crude product was purified by chromatography (EA/1% AcOH in hexanes)

Sources & evidence

ORD record
ord-8a65060469844aed85a0b97d89cccb9c
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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