trans-4-Fluoropyrrolidin-3-amine;dihydrochloride → trans-4-Fluoro-1-[6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-yl]pyrrolidin-3-amine

HRID 540221Notes

Reaction equation

HRID 540221 reaction equation
Cl[C:2]1[NH:11][C:10](=O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[S:14]1(=[O:25])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][NH:17][CH2:16][CH2:15]1.[F:26][C@@H:27]1[CH2:31][NH:30][CH2:29][C@H:28]1[NH2:32]>>[F:26][C@@H:27]1[CH2:31][N:30]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=3)[N:3]=[C:2]([N:17]3[CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[S:14](=[O:25])[CH2:15][CH2:16]3)[N:11]=2)[CH2:29][C@H:28]1[NH2:32]

Participants

4

Reactant 3

HCID 14612505trans-4-Fluoropyrrolidin-3-amine;dihydrochlorideHCID 196082032,3,4,5-Tetrahydrobenzo[f][1,4]thiazepine 1-oxideHCID 1355887902-Chloro-6-methyl-3,4-dihydroquinazolin-4-one

Product 1

HCID 86691411trans-4-Fluoro-1-[6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-yl]pyrrolidin-3-amine

Procedure

The title compound was prepared in analogy to Example 62-1 in Scheme 23 by using 2-chloro-6-methylquinazolin-4(3H)-one, 2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide and trans-4-fluoropyrrolidin-3-amine. MS obsd. (ESI+) [(M+H)+] 426. 1H NMR (400 MHz, CD3OD) 7.82 (s, 1 H), 7.71 (d, J=6.8 Hz, 1 H), 7.42 (m, 4 H), 5.26 (d, J=15.2 Hz, 1 H), 5.07 (d, J=51.2 Hz, 1 H), 4.78 (brs, 1 H), 4.43 (m, 2 H), 4.29 (m, 1 H), 4.06 (t, J=11.2 Hz, 1 H), 3.86 (d, J=12 Hz, 1 H), 3.75 (m, 1 H), 3.40 (m, 2 H), 2.40 (s, 3 H).

Sources & evidence

ORD record
ord-cb518493d42548158b1bbdc295966444
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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