Water → HCID 9878397, compound

HRID 494882Notes

Reaction equation

HRID 494882 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[CH:11][C:9]=2[CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.ClCCl>O1CCCC1>[NH2:1][CH2:4][CH2:5][C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[CH:11][C:9]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 22274506HCID 22274506, compound

Product 1

HCID 9878397HCID 9878397, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 162A was dissolved in 3 mL of tetrahydrofuran, and treated with triphenylphosphine (262 mg, 1 mmol) was added, along with 0.5 mL water. After 3 days, the reaction was poured into dichloromethane and washed with aqueous ammonia. The organic layer was purified by flash chromatography, eluting with 10-20% methanol/dichloromethane, (0.1% NH3) to give the title compound as a white powder. mp 118-120° C.; MS (DCI) m/z 263.0 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 3.00 (m, 2H), 3.08 (m, 2H), 6.64 (s, 1H), 7.56 (m, 2H), 7.82 (m, 5H).

Workup

  1. washwashed with aqueous ammonia
  2. customThe organic layer was purified by flash chromatography
  3. washeluting with 10-20% methanol/dichloromethane, (0.1% NH3)

Sources & evidence

ORD record
ord-370a8c7a0a7b4ea3ba427abe27c04669
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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