4-({4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}methyl)-3,4-difluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one → Isopropylamine

HRID 15167Notes

Reaction equation

HRID 15167 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:9]CN(CC2(F)C3=C(F)C=NC4C=CC(=O)N(C=43)C2)C[CH2:5]1.[O:26]1[C:35]2[CH:34]=[C:33]([CH2:36][NH:37][CH:38]3[CH2:43][CH2:42][N:41]([CH2:44][C:45]4([F:59])[C:49]5=[C:50]([F:58])[CH:51]=[N:52][C:53]6[CH:54]=[CH:55][C:56](=[O:57])[N:47]([C:48]=65)[CH2:46]4)[CH2:40][CH2:39]3)[N:32]=[CH:31][C:30]=2[O:29][CH2:28][CH2:27]1.[NH2:60][CH:61]1[CH2:66][CH2:65][N:64]([CH2:67][C:68]2([F:82])[C:72]3=[C:73]([F:81])[CH:74]=[N:75][C:76]4[CH:77]=[CH:78][C:79](=[O:80])[N:70]([C:71]=43)[CH2:69]2)[CH2:63][CH2:62]1>>[CH:4]([NH2:3])([CH3:9])[CH3:5].[O:26]1[C:35]2[CH:34]=[C:33]([CH2:36][NH:37][CH:38]3[CH2:43][CH2:42][N:41]([CH2:44][C:45]4([F:59])[C:49]5=[C:50]([F:58])[CH:51]=[N:52][C:53]6[CH:54]=[CH:55][C:56](=[O:57])[N:47]([C:48]=65)[CH2:46]4)[CH2:40][CH2:39]3)[N:32]=[CH:31][C:30]=2[O:29][CH2:28][CH2:27]1.[NH2:60][CH:61]1[CH2:62][CH2:63][N:64]([CH2:67][C:68]2([F:82])[C:72]3=[C:73]([F:81])[CH:74]=[N:75][C:76]4[CH:77]=[CH:78][C:79](=[O:80])[N:70]([C:71]=43)[CH2:69]2)[CH2:65][CH2:66]1

Participants

6

Reactant 3

HCID 236335464-({4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}methyl)-3,4-difluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneHCID 23634204HCID 23634204, compoundHCID 131728168(4R/S)-4-({4-amino-1-piperidinyl}methyl)-3,4-difluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one dihydrochloride

Product 3

HCID 6363IsopropylamineHCID 236335464-({4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-1-piperidinyl}methyl)-3,4-difluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneHCID 23634204HCID 23634204, compound

Procedure

4.3 g of the free base of (4R/S)-4-[(4-amino-1-piperidinyl)methyl]-3,4-difluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one dihydrochloride was resolved by preparative chiral HPLC into the two enantiomers E1 and E2 using a Cliralpak AD column, eluting with 50:50:0.1 acetonitrile:methanol:isopropylamine, affording enantiomers E1 (first eluting) and E2 (second eluting).

Workup

  1. washeluting with 50:50:0.1 acetonitrile

Sources & evidence

ORD record
ord-30e16d7de16b4a3991b33e489d3eaf00
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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