Diisopropylethylamine → HCID 25255105, compound

HRID 914138Notes

Reaction equation

HRID 914138 reaction equation
[F:1][C:2]1([F:33])[CH2:8][N:7]([CH:9]2[CH2:13][CH2:12][C@@H:11]([CH3:14])[CH2:10]2)[C:6]2[N:15]=[C:16]([NH:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][C:21]=3[O:29][CH3:30])[N:17]=[CH:18][C:5]=2[N:4]([CH3:31])[C:3]1=[O:32].[CH3:34][N:35]1[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[F:33][C:2]1([F:1])[CH2:8][N:7]([CH:9]2[CH2:13][CH2:12][C@@H:11]([CH3:14])[CH2:10]2)[C:6]2[N:15]=[C:16]([NH:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH:41][CH:38]4[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]4)=[O:26])=[CH:22][C:21]=3[O:29][CH3:30])[N:17]=[CH:18][C:5]=2[N:4]([CH3:31])[C:3]1=[O:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25255104HCID 25255104, compound

Product 1

HCID 25255105HCID 25255105, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the 4-(7,7-difluoro-5-methyl-9-((3R)-3-methylcyclopentyl)-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid, 1-methylpiperidin-4-amine (1.1 equivalent) and DIEA (3-6 equivalent) in 20 mL of anhydrous DMF, was added HATU (1.5 to 2 equivalent). The reaction mixture was stirred for 30 min. The reaction mixture was then diluted with ethyl acetate, washed with water and brine. The organic layer dried over Na2SO4 followed by HPLC purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96-1.06 (m, 3H) 1.06-2.12 (m, 13H) 2.16 (s, 3H) 2.77 (d, J=11.87 Hz, 2H) 3.32 (br. s., 3H) 3.65-3.80 (m, 1H) 3.93 (s, 3H) 3.97-4.12 (m, 2H) 4.73-4.96 (m, 1H) 7.44-7.52 (m, 2H) 7.97 (d, J=6.06 Hz, 1H) 8.12 (d, J=7.83 Hz, 1H) 8.25 (d, 2H). [M+H] calc'd for C28H37F2N7O3 558. found 558.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer dried over Na2SO4
  3. customfollowed by HPLC purification

Sources & evidence

ORD record
ord-c188eea37d4345d6861c56f69f3ff735
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

Loading…