Ammonia → HCID 86682367, compound

HRID 2283616Notes

Reaction equation

HRID 2283616 reaction equation
[F:1][C:2]([F:55])([F:54])[C:3]1C=[CH:5][C:6]([O:25][C:26]2[CH:31]=[C:30](F)[C:29]([S:33]([N:36](CC3C=CC(OC)=CC=3OC)[C:37]3[S:41][CH:40]=[N:39][N:38]=3)(=[O:35])=[O:34])=[CH:28][C:27]=2Cl)=[C:7]([C:9]2[N:13]([CH:14]3[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]3)[N:12]=[CH:11][CH:10]=2)[CH:8]=1.[F:56]C(F)(F)C(O)=O.O.N.Cl[CH2:66][Cl:67]>>[NH:16]1[CH2:17][CH:14]([N:13]2[C:9]([C:7]3([F:56])[CH:8]=[C:3]([C:2]([F:55])([F:54])[F:1])[C:66]([Cl:67])=[CH:5][CH:6]3[O:25][C:26]3[CH:31]=[CH:30][C:29]([S:33]([NH:36][C:37]4[S:41][CH:40]=[N:39][N:38]=4)(=[O:35])=[O:34])=[CH:28][CH:27]=3)=[CH:10][CH:11]=[N:12]2)[CH2:15]1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 962WaterHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68047229HCID 68047229, compound

Product 1

HCID 86682367HCID 86682367, compoundYield 88%

Procedure

tert-Butyl 3-{5-[5-trifluoromethyl-2-(2-chloro-4-{[(2,4-dimethoxybenzyl)(1,3,4-thiadiazol-5-yl)amino]sulfonyl}-5-fluorophenoxy)phenyl]-1H-pyrazol-1-yl}azetidine-1-carboxylate (Preparation 35, 590 mg, 0.72 mmol) was dissolved in dichloromethane (10 mL). Trifluoroacetic acid (2 mL) was added dropwise and the solution stirred at ambient temperature for 2.5 hours. The reaction mixture was concentrated in vacuo and the residue slurried in methanol (20 mL) before concentrating in vacuo again. This was repeated twice more. Finally the residue was again slurried in methanol (20 mL) and the solid removed by filtration. The filtrate was concentrated in vacuo to give a foam. Water (50 mL) was added followed by 0.880 aqueous ammonia (5 mL) to give a white solid which was collected by filtration, washed with methanol and dried in vacuo to afford the title compound as a white solid (360 mg, 88%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. concentrationbefore concentrating in vacuo again
  3. customthe solid removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a foam
  6. customto give a white solid which
  7. filtrationwas collected by filtration
  8. washwashed with methanol
  9. customdried in vacuo

Sources & evidence

ORD record
ord-91cb10774e7d45439538c262fc765a8d
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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