Dimethylformamide → HCID 10168470, compound

HRID 2085102Notes

Reaction equation

HRID 2085102 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[C:17]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH3:26])=[C:16]([O:27][CH2:28][C:29]#[C:30][CH2:31][OH:32])[N:15]=[C:14]([C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[N:13]=2)(=[O:10])=[O:9])=[N:6][CH:7]=1.[C:39]1([N:45]=[C:46]=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CN(C=O)C>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[N:13]=[C:14]([C:33]3[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=3)[N:15]=[C:16]([O:27][CH2:28][C:29]#[C:30][CH2:31][O:32][C:46](=[O:47])[NH:45][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:17]=2[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])(=[O:10])=[O:9])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 7672Phenyl isocyanateHCID 10302118HCID 10302118, compound

Product 1

HCID 10168470HCID 10168470, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 50 mg of 5-methyl-N-[6-(4-hydroxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimidinyl]-2-pyridine sulfonamide (Example 3), 10 mg of DMAP and 25 μl of phenylisocyanate in 5 ml of chloroform was refluxed for 15 minutes under argon. 1.5 ml of DMF was added and stirring and heating was continued for 16 h. The clear solution was diluted with 50 ml of ethyl acetate and washed with 50 ml of 10% aqueous citric acid and 2×50 ml of water. The organic phase was dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica gel eluting first with hexane:ethyl acetate 1:1, then with DCM containing 4% of methanol to give 47 mg of phenylcarbamic acid 4-[6-(5-methylpyridine-2-sulfonylamino)-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yloxy]-but-2-ynyl ester as a slightly yellow solid. LC-MS: tR=4.80 min, [M+1]+=653.37, [M−1]−=651.33.

Workup

  1. temperaturewas refluxed for 15 minutes under argon
  2. temperatureheating
  3. washwashed with 50 ml of 10% aqueous citric acid and 2×50 ml of water
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. customThe crude product was purified by column chromatography on silica gel eluting first with hexane:ethyl acetate 1:1

Sources & evidence

ORD record
ord-fe6f12c3ad3a4868a3166a716bdf0c8e
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

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