Diisopropylethylamine → HCID 25255105, compound

HRID 1880909Notes

Reaction equation

HRID 1880909 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, 3 H) 1.06-2.12 (m, 13 H) 2.16 (s, 3 H) 2.77 (d, J=11.87 Hz, 2 H) 3.32 (br. s., 3 H) 3.65-3.80 (m, 1 H) 3.93 (s, 3 H) 3.97-4.12 (m, 2 H) 4.73-4.96 (m, 1 H) 7.44-7.52 (m, 2 H) 7.97 (d, J=6.06 Hz, 1 H) 8.12 (d, J=7.83 Hz, 1 H) 8.25 (d, 2 H). [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-9ee22084a0a04680938720783ce88b1e
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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