Hydrochloric Acid → HCID 24875129, compound

HRID 1876931Notes

Reaction equation

C[O:2][C:3](=[O:31])[CH:4]([NH:19][C:20](=[O:30])[C:21]1[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=1[CH3:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][CH:14]=[C:15]([CH:17]=O)[CH:16]=2)=[CH:8][CH:7]=1.[CH3:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([NH2:39])[CH:34]=1.[Li+].[OH-].Cl>ClC(Cl)C.C(OCC)(=O)C>[CH3:32][C:33]1[CH:38]=[CH:37][N:36]=[C:35]([NH:39][CH2:17][C:15]2[CH:16]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([NH:19][C:20](=[O:30])[C:21]4[C:22]([CH3:29])=[CH:23][C:24]([CH3:28])=[CH:25][C:26]=4[CH3:27])[C:3]([OH:2])=[O:31])=[CH:7][CH:8]=3)[S:13][CH:14]=2)[CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

99 mg of (18) were dissolved in/ml of dichloroethane and 37 mg (1.5 eq.) of 4-methylpyridin-2-ylamine and 240 mg (5 eq.) of NaHB(OAc)3 were added. The solution was stirred for 2.5 h. After pouring in ethyl acetate the organic layer was washed with saturated NaHCO3, brine and dried over Na2SO4. The crude product was redissolved in 6 ml of 1,4-dioxane and 1 ml of water. The solution was cooled to 0° C. and 3 eq. of LiOH*H2O were added. The solution was neutralized after 6 h with 1 M HCl and concentrated in vacuo. The product was purified by HPLC to give 39.1 mg of (19) as TFA salt.

Workup

additionwere added
washwas washed with saturated NaHCO3, brine
dry with materialdried over Na2SO4
dissolutionThe crude product was redissolved in 6 ml of 1,4-dioxane
concentrationconcentrated in vacuo
customThe product was purified by HPLC

Sources & evidence

ORD record: ord-69b2a49396424dfe8a49c3606f381aea
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309735B2

Reaction notes

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