Dimethylformamide → HCID 86675066, compound

HRID 1500270Notes

Reaction equation

HRID 1500270 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2([CH2:20][CH2:19][N:18]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:17][CH2:16]2)[CH2:11]1.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:32]1[S:33][CH:34]=[C:35]([C:37](O)=[O:38])[N:36]=1.C(N(CC)C(C)C)(C)C.CN(C=[O:53])C>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][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:38])=[C:3]([N:10]2[CH2:15][CH2:14][CH2:13][C:12]3([CH2:16][CH2:17][N:18]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:19][CH2:20]3)[CH2:11]2)[CH:4]=1)(=[O:53])[NH2:7]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27763172-(Thiophen-2-yl)-1,3-thiazole-4-carboxylic acidHCID 86675067HCID 86675067, compound

Product 1

HCID 86675066HCID 86675066, compound

Procedure

To Intermediate 4-Amino-3-[9-(2,2,2-trifluoro-acetyl)-2,9-diaza-spiro[5.5]undec-2-yl]-benzonitrile was added 2-thiophen-2-yl-thiazole-4-carboxylic acid (098 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 {4-carbamoyl-2-[9-(2,2,2-trifluoro-acetyl)-2,9-diaza-spiro[5.5]undec-2-yl]-phenyl}-amide. HPLC-MS RT=4.46 min, mass calculated for formula C26H26F3N5O3S2 577.14, observed LCMS m/z 578.21 (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-918e10c3dd114ad697d6741e7d1f49cd
Source dataset
uspto-grants-2015_12
Patent number
US09206142B2

Reaction notes

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