Hydrochloric Acid → HCID 16062722, compound

HRID 507290Notes

Reaction equation

HRID 507290 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[S:11][CH:12]=[C:13]([C:15]([OH:17])=O)[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl:41][C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C.C(N(CC)CC)C>[Cl:41][C:42]1[CH:48]=[CH:47][C:45]([NH:46][C:15]([C:13]2[N:14]=[C:10]([CH:7]3[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]3)[S:11][CH:12]=2)=[O:17])=[CH:44][CH:43]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68460887HCID 68460887, compound

Product 1

HCID 16062722HCID 16062722, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 29.1 mg (0.1 mmol) 2-(1-isopropyl-piperidin-4-yl)-thiazole-4-carboxylic acid; hydrochloride, 35.3 mg (0.11 mmol) 2-(1H-benzotriazol-1-yl-1,1,3,3-tetramethyl uronium tetrafluoroborate, 14.03 mg (0.11 mol) 4-chloroaniline and 140 ul (0.5 mmol) N-ethyldiisopropylamine in 1 ml DMF was reacted at room temperature for a prolonged period of time. The mixture was treated with 50 μl triethylamine and subjected to preparative HPLC purification on reversed phase material eluting with a gradient of acetonitrile/water/triethyamine (0.05%). The product fractions were evaporated to dryness to yield 10.6 mg (29%) of the title compound. MS (m/e): 364.1 (MH+, 100%).

Workup

  1. customsubjected to preparative HPLC purification on reversed phase material
  2. washeluting with a gradient of acetonitrile/water/triethyamine (0.05%)
  3. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-e3469154ca6d40bc9bfd33f514230714
Source dataset
uspto-grants-2010_08
Patent number
US07786143B2

Reaction notes

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