Dimethylamine → HCID 20430311, compound

HRID 1014163Notes

Reaction equation

HRID 1014163 reaction equation
Br[CH2:2]C(Cl)=O.[C:6](Cl)(=O)[CH:7]=[CH2:8].CN(C(ON1N=N[C:21]2[CH:22]=[CH:23][CH:24]=[N:25][C:20]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:37]([CH:41]([CH3:43])C)[CH:38]([CH3:40])[CH3:39].N(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[NH:25]([N:37]1[C:38]2[C:39](=[CH:6][CH:7]=[CH:8][CH:40]=2)[CH2:43][CH2:41]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:2]=1

Participants

8

Reactant 5

HCID 674DimethylamineHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 20430311HCID 20430311, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate XVI is subjected to subsequent acylation with an acylating agent, e.g. α-bromoacetyl chloride, acryloyl chloride, or an amino acid, with coupling reagents, e.g. HATU, DMAP, and base, e.g. PS-DIPEA, and solvent, e.g. THF. The acylating agent may be reacted with an appropriate amine base, e.g. Me2NH (with solvent, e.g. THF), and the product then reduced (see reduction of IVa, scheme 4) to provide anilino indoline tails IVx.

Sources & evidence

ORD record
ord-9d2eea0524b0446e86eb8dde3a266699
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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