Ethanol → HCID 178457732, compound

HRID 2059728Notes

Reaction equation

C1N=CN([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])C=1.[CH3:13][N:14](C=O)C.[C:18]([NH2:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:20])[CH3:19].CC[N:30]([CH2:33][CH3:34])CC.C[CH2:36][OH:37]>>[OH:7][C:6]1[C:34]([C:36]([NH:27][C:18]([CH3:20])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:19])=[O:37])=[CH:33][N:30]=[C:12]([N:11]2[CH:10]=[CH:9][CH:13]=[N:14]2)[N:8]=1

Participants

Reactant 5

HCID 702Ethanol

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 682631,1'-Carbonyldiimidazole

HCID 68509Cumylamine

Product 1

HCID 178457732HCID 178457732, compound

Conditions

Temperature: 77 °C

Procedure

The product of Intermediate 10 (8.00 g, 38.8 mmol) was combined with CDI (7.24 g, 44.6 mmol) and DMF (80 mL). The reaction was aged at 105° C. for 45 min and cooled to about 77° C. Cumyl amine (7.26 mL, 50.4 mmol) and NEt3 (5.41 mL, 38.8 mmol) were added and the reaction continued to age at 77° C. for an additional 5 h. The reaction was concentrated and then diluted with CH2Cl2 and washed with aq. HCl (2 M) and water. The organic portion was concentrated and suspended in Et2O (270 mL) and aged for 1 h 40 min before the product was isolated by filtration. The solid was then suspended in 10% EtOH/90% Et2O (200 mL) and aged about 16 hrs before it was isolated by filtration and dried to afford the title compound. HPLC/MS: 342.1 (M+1); Rt=2.66 min.

Workup

waitthe reaction continued to age at 77° C. for an additional 5 h
concentrationThe reaction was concentrated
additiondiluted with CH2Cl2
washwashed with aq. HCl (2 M) and water
concentrationThe organic portion was concentrated
waitaged for 1 h 40 min before the product
customwas isolated by filtration
customwas isolated by filtration
customdried

Sources & evidence

ORD record: ord-be9b024bdc43480ea11706d008c89a04
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278304B2

Reaction notes

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