Diisopropylethylamine → HCID 178511274, compound

HRID 1257705Notes

Reaction equation

HRID 1257705 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[N:16])[CH2:11][CH2:10]1.[C:17]1([S:23]([N:26]2[C:30]3=[N:31][CH:32]=[C:33]([N+:36]([O-:38])=[O:37])[C:34](Cl)=[C:29]3[CH:28]=[CH:27]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[C:17]1([S:23]([N:26]2[C:30]3=[N:31][CH:32]=[C:33]([N+:36]([O-:38])=[O:37])[C:34]([NH:8][C@H:9]4[CH2:14][CH2:13][C@H:12]([C:15]#[N:16])[CH2:11][CH2:10]4)=[C:29]3[CH:28]=[CH:27]2)(=[O:24])=[O:25])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 583947741-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo(2,3-b)pyridineHCID 178511280HCID 178511280, compound

Product 1

HCID 178511274HCID 178511274, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of trans 4-amino-cyclohexanecarbonitrile trifluoroacetic acid salt (6.36 g, 26.7 mmol), 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (8.21 g, 24.3 mmol) and diisopropylethylamine (12.5 mL, 73.0 mmol) in propan-2-ol (200 mL) was heated at reflux for 3 hours. The cooled mixture was filtered and the precipitate washed with propan-2-ol to afford 9.04 g (87%) of trans 4-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclohexanecarbonitrile as a bright yellow solid. LCMS (Method Q, ESI): RT=4.15 min, m+H=426.0; 1H NMR (400 MHz, CDCl3) δ: 9.11 (s, 1H), 9.07 (d, 1H), 8.20 (m, 2H), 7.63 (m, 2H), 7.53 (m, 2H), 6.67 (d, 1H), 4.06 (m, 1H), 2.66 (m, 1H), 2.24 (m, 4H), 1.83 (m, 2H), 1.58 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe cooled mixture was filtered
  4. washthe precipitate washed with propan-2-ol

Sources & evidence

ORD record
ord-6e71b06534bc43438d91288ae1f832a5
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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