Methanol → HCID 86626618, compound

HRID 1747199Notes

Reaction equation

HRID 1747199 reaction equation
[NH:1]([C:3](=[O:11])[CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH2:10])=[S:9])[NH2:2].C(N([CH2:17][CH3:18])CC)C.OC1OC(C2[CH:26]=[C:27]([NH:31][C:32]([NH2:34])=[S:33])[CH:28]=[CH:29][CH:30]=2)=NN=1.C[OH:36]>>[NH:1]([C:3](=[O:11])[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[S:9][CH:30]=[C:29]([C:28]2[S:33][C:32]([NH:34][C:17](=[O:36])[CH3:18])=[N:31][C:27]=2[CH3:26])[N:10]=1)[NH2:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 86626617HCID 86626617, compoundHCID 178514161HCID 178514161, compound

Product 1

HCID 86626618HCID 86626618, compound

Conditions

Temperature
0 °C

Procedure

N-(4-hydrazino-4-oxobutyl)thiourea (128.50 mg; 0.73 mmol; 1.00 eq.) is dissolved in MeOH (7.00 ml) and triethylamine (0.30 ml; 2.19 mmol; 3.00 eq.). The solution is cooled down to 0° C. and intermediate 1 (201.20 mg; 0.73 mmol; 1.00 eq.) is added as a solid. The mixture is stirred 2 hours at RT. Solvents are evaporated and N-{2-[(4-hydrazino-4-oxobutyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide is used in the next step without further purification. M− (ESI): 353; M+ (ESI): 355. HPLC, Rt: 1.19 min (purity: 95.3%).

Workup

  1. customSolvents are evaporated
  2. customN-{2-[(4-hydrazino-4-oxobutyl)amino]-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl}acetamide is used in the next step without further purification

Sources & evidence

ORD record
ord-7b6b101866694cfebc93e979ffc6dd2c
Source dataset
uspto-grants-2015_10
Patent number
US09150561B2

Reaction notes

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