Diisopropylethylamine → HCID 46913023, compound

HRID 405942

Reaction equation

HRID 405942 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]([O:24][C:25]4[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=4)[CH2:20][CH2:19]3)=[N:6][C:5]=2[CH2:4][CH2:3]1.C([N:37]([CH:40]([CH3:42])[CH3:41])[CH2:38]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:40]1([N:37]([CH3:38])[C:29](=[O:30])[C:28]2[CH:27]=[CH:26][C:25]([O: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:33][CH:32]=2)[CH2:41][CH2:42]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 469128454-{1-[5-oxo-4-(tetrahydropyran-4-ylamino)-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-2-yl]-piperidin-4-yloxy}-benzoic acid

Product 1

HCID 46913023HCID 46913023, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

55 mg of Example 184 (see 40.) are placed in 2 ml dimethylformamide, then 81 l diisopropylethylamine and 53.1 mg O-(7-azabenzotriazol-1-yl-)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) are added. After 15 min 13.8 mg cyclopropylmethylamine hydrochloride are 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). 30 mg of Example 242 are obtained as a solid.

Workup

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

Sources & evidence

ORD record
ord-f5998a79fbcc4c73bfae8095fdc14141
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Linked notes

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