HCID 18320744, compound → HCID 18320732, compound

HRID 1699523Notes

Reaction equation

HRID 1699523 reaction equation
[C:1]([C:4]1[NH:5][C:6](=[O:46])[N:7]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:33]=2)[C:8]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][CH2:20][N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])[CH:10]=1)(=O)[NH2:2]>C(Cl)Cl>[C:1]([C:4]1[NH:5][C:6](=[O:46])[N:7]([C:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:33]=2)[C:8]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][CH2:20][N:21]2[C:22](=[O:31])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]2=[O:30])[CH:10]=1)#[N:2]

Participants

3

Reactant 1

HCID 18320744HCID 18320744, compound

Product 1

HCID 18320732HCID 18320732, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To 0.10 g (0.16 mmol) of the product of step f) was added 10 ml of a solution of TMS-polyphosphate (Yokoyama et al. Synthesis (1982) 591-592) in CH2Cl2. The flask was sealed and heated on an oil bath to 50° C. for 3 hours. The organic phase was diluted to 20 ml with CH2Cl2 and then washed with 10 ml of water, 5 ml of 1M sulfuric acid and finally with 5 ml of brine. The organic phase was evaporated, and the residue was purified by chromatography on silica (CH2Cl2:MeOH 97:3), furnishing 65 mg (67%) of the sub-title product.

Workup

  1. customThe flask was sealed
  2. washwashed with 10 ml of water, 5 ml of 1M sulfuric acid and finally with 5 ml of brine
  3. customThe organic phase was evaporated
  4. customthe residue was purified by chromatography on silica (CH2Cl2:MeOH 97:3)

Sources & evidence

ORD record
ord-816bc3db98b34062a6c654f1a02e4d09
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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