Diisopropylethylamine → HCID 58117637, compound

HRID 405944

Reaction equation

HRID 405944 reaction equation
[O:1]=[S:2]1[C:10]2[C:9]([NH:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=4)[C:27](O)=[O:28])[CH2:20][CH2:19]3)=[N:6][C:5]=2[CH2:4][CH2:3]1.C([N:36]([CH:39]([CH3:41])[CH3:40])[CH2:37]C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.C1(CN)CC1>CN(C)C=O>[CH:39]1([N:36]([CH3:37])[C:27](=[O:28])[C:26]2[CH:30]=[CH:31][CH:32]=[C:24]([CH:21]3[CH2:20][CH2:19][N:18]([C:7]4[N:8]=[C:9]([NH:11][CH:12]5[CH2:17][CH2:16][O:15][CH2:14][CH2:13]5)[C:10]5[S:2](=[O:1])[CH2:3][CH2:4][C:5]=5[N:6]=4)[CH2:23][CH2:22]3)[CH:25]=2)[CH2:40][CH2:41]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58117546HCID 58117546, compound

Product 1

HCID 58117637HCID 58117637, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

59.8 mg 3-{1-[5-oxo-4-(tetrahydropyran-4-ylamino)-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-2-yl]-piperidin-4-yl}-benzoic acid are placed in 2.3 ml dimethylformamide, then 91 l diisopropylethylamine and 60 mg O-(7-azabenzotriazol-1-yl-)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) are added. After 15 min a mixture of 15.5 mg cyclopropylmethylamine hydrochloride in 300 l dimethylformamide is added. The reaction mixture is stirred at ambient temperature until there is no further reaction, and the product is purified directly by preparative HPLC (method B). 50 mg Example 249 are obtained as a solid. Analytical HPLC-MS (method D): RT=1.05 min.

Workup

  1. additionis added
  2. customno further reaction
  3. customthe product is purified directly by preparative HPLC (method B)

Sources & evidence

ORD record
ord-fcb79a69383b461ba1f1519ec6a1cf14
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Linked notes

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