Ammonium Chloride → HCID 90370185, compound

HRID 2176056Notes

Reaction equation

HRID 2176056 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[N:11]1([CH2:17][C:18]2[CH:19]=[C:20]([C:24]3[O:25][C:26](=[O:37])[C:27]4[C:32]5[CH2:33][CH2:34][CH2:35][CH2:36][C:31]=5[S:30][C:28]=4[N:29]=3)[CH:21]=[CH:22][CH:23]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[CH:38]1([C:41]2[S:45][C:44]([NH2:46])=[N:43][N:42]=2)[CH2:40][CH2:39]1.[Cl-].[NH4+]>C(Cl)(Cl)Cl.C1COCC1>[CH:38]1([C:41]2[S:45][C:44]([NH:46][C:26]([C:27]3[C:32]4[CH2:33][CH2:34][CH2:35][CH2:36][C:31]=4[S:30][C:28]=3[NH:29][C:24](=[O:25])[C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)[CH:19]=3)=[O:37])=[N:43][N:42]=2)[CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 7170215-Cyclopropyl-1,3,4-thiadiazol-2-amineHCID 2733832Lithium HexamethyldisilazideHCID 90370056HCID 90370056, compound

Product 1

HCID 90370185HCID 90370185, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 0.07 mL of lithium hexamethyldisilazide (1.0M in THF) and 0.2 mL of THF was added to a mixture of 11.5 mg of 2-[3-(morpholin-4-ylmethyl)phenyl]-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-4-one, 4.9 mg of 5-cyclopropyl-1,3,4-thiadiazol-2-amine, and 0.8 mL of THF, followed by stirring overnight at room temperature. Chloroform and a saturated aqueous ammonium chloride solution were added to the reaction mixture, and the organic layer was separated. After the solvent was removed under reduced pressure, the obtained residue was purified, thereby obtaining 11.4 mg of N-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-2-{[3-(morpholin-4-ylmethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide.

Workup

  1. customthe organic layer was separated
  2. customAfter the solvent was removed under reduced pressure
  3. customthe obtained residue was purified

Sources & evidence

ORD record
ord-ac2dd9c9848b4a909bbbf534b1f824c5
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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