Hydrochloric Acid → 4-cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-5-carboxylic acid

HRID 634308Notes

Reaction equation

HRID 634308 reaction equation
[CH:1]1([C:4]2[C:9]([C:10]([O:12]C)=[O:11])=[CH:8][N:7]=[C:6]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]5[O:24][C:25]([NH:28][CH:29]([CH3:31])[CH3:30])=[N:26][N:27]=5)[CH:21]=4)[N:16]([S:32]([C:35]4[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=4)(=[O:34])=[O:33])[CH:15]=3)[N:5]=2)[CH2:3][CH2:2]1.C1COCC1.O.[OH-].[Li+].Cl>O>[CH:1]1([C:4]2[C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=[C:6]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]5[O:24][C:25]([NH:28][CH:29]([CH3:31])[CH3:30])=[N:26][N:27]=5)[CH:21]=4)[N:16]([S:32]([C:35]4[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=4)(=[O:33])=[O:34])[CH:15]=3)[N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68328004HCID 68328004, compound

Product 1

HCID 683286994-cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-cyclopropyl-2-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)pyrimidine-5-carboxylate (110 mg, 0.192 mmol) was treated with THF (2 mL), water (1.0 mL) and lithium hydroxide monohydrate (20 mg, 0.48 mmol) and stirred at RT for 1.5 h. The reaction mixture was treated with a 5 N HCl (0.5 mL) and concentrated on the rotovap. It was then dried further by azeotroping with toluene and drying under high vacuum at 50° C. for 3 h. MS (ESI, pos. ion) m/z: 559.0 (M+H)+. It was then used in the subsequent step with further purification.

Workup

  1. concentrationconcentrated on the rotovap
  2. customIt was then dried further
  3. customby azeotroping with toluene
  4. customdrying under high vacuum at 50° C. for 3 h
  5. customIt was then used in the subsequent step with further purification

Sources & evidence

ORD record
ord-77b2e696054c4d599e950d05d5de1023
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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