Dimethylformamide → HCID 25098060, compound

HRID 1500269Notes

Reaction equation

HRID 1500269 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[C:22]([C:24]#N)[CH:21]=[CH:20][C:19]=3[NH2:26])[CH2:13]2)C1)=O)(C)(C)C.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:32]1[S:33][CH:34]=[C:35]([C:37]([OH:39])=O)[N:36]=1.C(N(CC)C(C)C)(C)C.C[N:50]([CH:52]=[O:53])C>>[NH2:8][CH2:12][CH2:11][CH:10]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[CH:23]=[C:22]([CH2:24][C:52](=[O:53])[NH2:50])[CH:21]=[CH:20][C:19]=2[NH:26][C:37]([C:35]2[N:36]=[C:32]([C:28]3[S:27][CH:31]=[CH:30][CH:29]=3)[S:33][CH:34]=2)=[O:39])[CH2:13]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27763172-(Thiophen-2-yl)-1,3-thiazole-4-carboxylic acidHCID 68856329HCID 68856329, compound

Product 1

HCID 25098060HCID 25098060, compound

Procedure

To the solution of 7-(2-Amino-5-cyano-phenyl)-2,7-diaza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester was added 2-thiophen-2-yl-thiazole-4-carboxylic acid (product of step 2, 0.98 eq,) in DMF (1 mL). Then, a solution of N,N-diisopropylethylamine (1.5 eq) HATU (1.5 eq) was added. The resulting reaction was stirred at room temperature for 15 hours and then concentrated and treated with 3 mL of (4:1) TFA:H2SO4. The reaction mixture was concentrated and purified using reverse phase HPLC to provide 2-Thiophen-2-yl-thiazole-4-carboxylic acid {2-[3-(2-amino-ethyl)-piperidin-1-yl]-4-carbamoylmethyl-phenyl}-amide. HPLC-MS RT=3.13 min, mass calculated for formula C23H25N5O2S2 467.14, observed LCMS m/z 468.21 (M+H).

Workup

  1. customThe resulting reaction
  2. concentrationconcentrated
  3. additiontreated with 3 mL of (4:1) TFA
  4. concentrationThe reaction mixture was concentrated
  5. custompurified

Sources & evidence

ORD record
ord-0dae83fc17c3496b897b817093a74088
Source dataset
uspto-grants-2015_12
Patent number
US09206142B2

Reaction notes

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