Ammonia → HCID 68328641, compound

HRID 634331Notes

Reaction equation

HRID 634331 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[O:21][C:22]([NH:25][CH:26]([CH3:28])[CH3:27])=[N:23][N:24]=3)[CH:18]=2)[N:13]([S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:12]=1)[C:5](O)=[O:6].CC[N:41]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.N>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[O:21][C:22]([NH:25][CH:26]([CH3:27])[CH3:28])=[N:23][N:24]=3)[CH:18]=2)[N:13]([S:29]([C:32]2[CH:33]=[CH:34][C:35]([CH3:36])=[CH:37][CH:38]=2)(=[O:30])=[O:31])[CH:12]=1)[C:5]([NH2:41])=[O:6]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68328233HCID 68328233, compound

Product 1

HCID 68328641HCID 68328641, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluoro-4-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)benzoic acid (500 mg, 0.936 mmol) in DMF (10 mL) was added EDC HCl (269 mg, 1.40 mmol) followed by HOBt and NH3 (284 mg, 1.87 mmol). The reaction was stirred at RT for 1 h, then quenched with ice cold water (20 mL) to get a precipitate. The precipitate was filtered, washed with water (2×100 mL) and dried to give the crude product (250 mg). MS (ESI, pos. ion) m/z: 534.1 (M+1).

Workup

  1. customquenched with ice cold water (20 mL)
  2. customto get a precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with water (2×100 mL)
  5. customdried

Sources & evidence

ORD record
ord-ccd906ca1a57415982e431f94dfa2476
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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