Beta-Alanine → N-({[4-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)-beta-alanine

HRID 1715287Notes

Reaction equation

HRID 1715287 reaction equation
C[C:2]1[N:3]=[C:4]([NH:20][C:21]([N:23]2[CH:27]=[CH:26]N=C2)=[O:22])[S:5][C:6]=1[C:7]1[N:8]=[C:9]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[S:10][CH:11]=1.NCC[C:31]([OH:33])=[O:32].[CH2:34](N(CC)CC)C>CN(C=O)C>[CH3:34][C:7]1([C:6]2[S:5][C:4]([NH:20][C:21]([NH:23][CH2:27][CH2:26][C:31]([OH:33])=[O:32])=[O:22])=[N:3][CH:2]=2)[CH2:11][S:10][C:9]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[N:8]1

Participants

5

Reactant 3

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 59465567N-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]-1H-imidazole-1-carboxamide

Product 1

HCID 86621996N-({[4-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)-beta-alanineYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-[4′-methyl-2-(morpholin-4-ylcarbonyl)-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide, prepared as in Step 3 of Example 36, described above (75 mg; 0.19 mmol; 1 eq.), is added DMF (3 ml), Beta-alanine (Aldrich) (18.2 mg; 0.20 mmol; 1.10 eq.) and triethylamine (57 μl; 0.41 mmol; 2.20 eq.). The mixture is stirred 3 days at rt. Solvents are evaporated and the crude product is crystallized in MeOH, affording Compound (47) as a light yellow solid (17 mg; 22%). 1H NMR (DMSO-d6, 300 MHz) δ 2.41 (s, 3H), 2.49 (m, 4H), 3.31 (m, 6H), 4.33 (m, 2H), 6.71 (br s, 1H), 7.90 (s, 1H), 10.47 (br s, 1H), 12.34 (br s, 1H). M− (ESI): 424.03; M+ (ESI): 426.08. HPLC (method A), Rt: 2.20 min (purity: 98%).

Workup

  1. customSolvents are evaporated
  2. customthe crude product is crystallized in MeOH

Sources & evidence

ORD record
ord-f6ea04e38b48428f80b234fdaa038195
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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