Acetonitrile → HCID 86762201, compound

HRID 1919009Notes

Reaction equation

HRID 1919009 reaction equation
[P:1]([O:13][CH2:14][C:15]1[C:20]([CH:21]2[C:26]3[S:27][C:28]4[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29]=4[C:25]=3[CH2:24][CH2:23][NH:22]2)=[CH:19][CH:18]=[CH:17][C:16]=1[C:35]1[CH:40]=[C:39]([NH:41][C:42]2[CH:47]=[CH:46][N:45]=[CH:44][N:43]=2)[C:38](=[O:48])[N:37]([CH3:49])[CH:36]=1)([O:8]CCC#N)([O:3]CCC#[N:7])=[O:2].C(#[N:52])C>C(N(CC)CC)C>[P:1]([O-:3])([O-:8])([O:13][CH2:14][C:15]1[C:20]([CH:21]2[C:26]3[S:27][C:28]4[CH2:32][C:31]([CH3:33])([CH3:34])[CH2:30][C:29]=4[C:25]=3[CH2:24][CH2:23][NH:22]2)=[CH:19][CH:18]=[CH:17][C:16]=1[C:35]1[CH:40]=[C:39]([NH:41][C:42]2[CH:47]=[CH:46][N:45]=[CH:44][N:43]=2)[C:38](=[O:48])[N:37]([CH3:49])[CH:36]=1)=[O:2].[NH4+:7].[NH4+:52]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 67016332HCID 67016332, compound

Product 1

HCID 86762201HCID 86762201, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with 216a (450 mg, 0.631 mmol) and acetonitrile (8 mL), and the mixture was cooled to 0° C. Triethylamine (4 mL) was added followed bis trimethyl-silyl trifluoroacetamide (4 mL), and the mixture was stirred at room temperature for 40 h. After this time, the mixture was concentrated under reduced pressure and the resulting residue was purified by flash column chromatography (silica, 40:20:40 chloroform/methanol/ammonia) to afford 216b in 52% yield (210 mg) as an amorphous yellow solid: mp 260-262° C. d; 1H NMR (500 MHz, DMSO-d6) d 9.12 (s, 1H), 8.66 (s, 1H), 8.62 (d, J=2.0 Hz, 1H), 8.27 (d, J=4.0 Hz, 1H), 7.54 (s, 1H), 7.43 (t, J=7.5 Hz, 1H), 7.32-7.27 (m, 3H), 7.15 (br s, 2H), 4.69 (d, J=9.0 Hz, 1H), 4.46 (d, J=7.0 Hz, 1H), 3.87-3.83 (m, 3H), 3.57 (s, 3H), 3.36-3.17 (br s, 8H), 2.77-2.63 (m, 3H), 1.23 (s, 3H), 1.21 (s, 3H); MS (ESI+) m/z 608.2 (M+H for C29H30N5O6PS).

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. concentrationAfter this time, the mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by flash column chromatography (silica, 40:20:40 chloroform/methanol/ammonia)

Sources & evidence

ORD record
ord-35ea8fd7700545d59827810df54aa418
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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