Ammonia → HCID 86717776, compound

HRID 1468820Notes

Reaction equation

HRID 1468820 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][O:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[N:9][CH:10]=1)(=[O:4])=[O:3].FC(F)(F)C(O)=O.N>ClCCl.CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][O:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:9][CH:10]=1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 86717777HCID 86717777, compound

Product 1

HCID 86717776HCID 86717776, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

The product of step D (207 mg, 0.488 mmol) was dissolved in dichloromethane (1.63 mL) and trifluoroacetic acid (1.62 mL, 21.0 mmol) was added. At 1.75 h the volatiles were removed to yield an oil, which was dissolved in 1 mL of MeOH and 1.5 mL of 7 M NH3 in MeOH. After 30 min all volatiles were removed. The free base was used without further purification. 1H NMR (500 MHz, CDCl3) δ 9.10 (d, 1H), 8.26 (dd, 1H), 7.68 (d, 1H), 4.78 (d, 1H), 4.71 (d, 1H), 3.89-3.84 (m, 1H), 3.53-3.49 (m, 1H), 3.46-3.41 (m, 1H), 3.15 (s, 3H), 2.93-2.81 (m, 2H), 2.19-2.12 (m, 1H), 2.02-1.94 (m, 1H), 1.80-1.68 (m, 2H), 1.80-1.68 (m, 2H), 1.38-1.30 (m, 1H), 1.19-1.09 (m, 1H), 0.89-0.22 (m, 2H), 0.11-0.06 (m, 1H). MS (ESI) m/z 437 [M+H]+.

Workup

  1. customAt 1.75 h the volatiles were removed
  2. customto yield an oil, which
  3. customAfter 30 min all volatiles were removed
  4. customThe free base was used without further purification

Sources & evidence

ORD record
ord-0e22ccafacde46fb925cb94bfb01bc44
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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