Formaldehyde → HCID 178486517, compound

HRID 2170773Notes

Reaction equation

HRID 2170773 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:17]3[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:18][CH:19]([CH3:21])[CH3:20])[CH:16]=3)[CH2:11][C:10](=[O:24])[N:9]2[C:25]2[N:30]=[CH:29][C:28]([N:31]([CH2:33][C@H:34]3[CH2:39][CH2:38][C@H:37]([NH:40][CH2:41][C:42]([NH:44][CH3:45])=[O:43])[CH2:36][CH2:35]3)[CH3:32])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.[CH2:46]=O>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:17]3[C:12](=[CH:13][C:14]([O:22][CH3:23])=[C:15]([O:18][CH:19]([CH3:20])[CH3:21])[CH:16]=3)[CH2:11][C:10](=[O:24])[N:9]2[C:25]2[CH:26]=[CH:27][C:28]([N:31]([CH3:32])[CH2:33][C@H:34]3[CH2:35][CH2:36][C@H:37]([N:40]4[CH2:41][C:42](=[O:43])[N:44]([CH3:46])[CH2:45]4)[CH2:38][CH2:39]3)=[CH:29][N:30]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 178485790HCID 178485790, compound

Product 1

HCID 178486517HCID 178486517, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of Example 122 (38 mg, 0.061 mmol) and formaldehyde (0.046 ml, 37% solution, 10 eq, 0.612 mmol) was heated for 15 h in EtOH (1 mL) at 80° C. The reaction mixture was concentrated to dryness and the residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/[DCM/MeOH 9:1] 1:0→0:1) yielding the title compound as a colorless solid (31 mg, 0.048 mmol, 79%). HPLC: FtRet=1.236; LC-MS: m/z 646.4 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/[DCM/MeOH 9:1] 1:0→0:1)

Sources & evidence

ORD record
ord-0018e27e222747859d6101f9d5f3428a
Source dataset
uspto-grants-2015_06
Patent number
US09051279B2

Reaction notes

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