Methylamine → HCID 178485518, compound

HRID 1014568Notes

Reaction equation

Cl.Cl[C:3]1[N:16]2[C:7](=[N:8][C:9]3[C:14]([C:15]2=[O:17])=[C:13]([F:18])[CH:12]=[CH:11][CH:10]=3)[C:6]2[CH:19]=[CH:20][N:21](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]=2[N:4]=1.[CH3:32][N:33]([CH2:35][C:36]([N:38]1[C:46]2[C:41](=[CH:42][C:43]([N:48]([CH3:50])[CH3:49])=[C:44]([NH2:47])[CH:45]=2)[CH2:40][CH2:39]1)=[O:37])[CH3:34].[CH3:51][NH2:52]>>[CH3:49][N:48]([CH3:50])[C:43]1[CH:42]=[C:41]2[C:46](=[CH:45][C:44]=1[NH:47][C:3]1[NH:4][C:5]3=[N:21][CH:20]=[CH:19][C:6]3=[C:7]([NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([F:18])[C:14]=3[C:15]([NH:52][CH3:51])=[O:17])[N:16]=1)[N:38]([C:36](=[O:37])[CH2:35][N:33]([CH3:32])[CH3:34])[CH2:39][CH2:40]2

Participants

Reactant 3

HCID 6329Methylamine

HCID 59441925HCID 59441925, compound

HCID 673162535-chloro-8-fluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2',3':4,5]pyrimido[6,1-b]quinazolin-7(3H)-one HCl salt

Product 1

HCID 178485518HCID 178485518, compoundYield 44%

Procedure

In a manner analogous to a procedure outlined previously, 2-[(2-{[5-(dimethylamino)-1-(N,N-dimethylglycyl)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide was prepared from 5-chloro-8-fluoro-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one hydrochloride, 1-[(dimethylamino)acetyl]-N5,N5-dimethyl-2,3-dihydro-1H-indole-5,6-diamine, and methyl amine to afford the title compound (0.20 g, 44% over 3 steps). ESIMS (M+H)+=546. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 6 H) 2.58 (s, 6H) 2.81 (d, J=3.61 Hz, 3 H) 3.02-3.14 (m, 2 H) 3.18 (s, 211) 4.16 (t, J=8.23 Hz, 2 H) 6.27 (br. s., 1 H) 6.87-6.99 (m, 2 H) 7.06 (s, 1 H) 7.32-7.45 (m, 1 H) 7.66 (s, 1 H) 8.38 (d, J=8.23 Hz, 1 H) 8.56 (br. s., 1 H) 8.77 (s, 1H) 10.17 (s, 1 H) 11.30 (br. s., 1H).

Sources & evidence

ORD record: ord-5544f8f351134f9f97e766af81d3296d
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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