2-Fluoropropane-1,3-diamine → 2-Fluoro-N-[6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)thieno[3,2-d]pyrimidin-4-yl]propane-1,3-diamine

HRID 1910455Notes

Reaction equation

HRID 1910455 reaction equation
[O:1]=[S:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[NH:14][C:15](=O)[C:16]3[S:21][C:20]([CH3:22])=[CH:19][C:17]=3[N:18]=2)[CH2:4][CH2:3]1.[F:24][CH:25]([CH2:28][NH2:29])[CH2:26][NH2:27]>>[F:24][CH:25]([CH2:28][NH2:29])[CH2:26][NH:27][C:15]1[C:16]2[S:21][C:20]([CH3:22])=[CH:19][C:17]=2[N:18]=[C:13]([N:5]2[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[S:2](=[O:1])[CH2:3][CH2:4]2)[N:14]=1

Participants

3

Reactant 2

HCID 199026462-Fluoropropane-1,3-diamineHCID 1363597882-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 715487852-Fluoro-N-[6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)thieno[3,2-d]pyrimidin-4-yl]propane-1,3-diamine

Procedure

The title compound was prepared in analogy to Example 3-1 in Scheme 3 by using 2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylthieno[3,2-d]pyrimidin-4(3H)-one and 2-fluoro-1,3-propanediamine. MS obsd. (ESI+) [(M+H)+] 420, 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.73 (d, J=6.6 Hz, 1H), 7.68 (d, J=6.8 Hz, 1H), 7.39-7.51 (m, 2H), 6.81 (s, 1H), 5.19 (d, J=14.7 Hz, 1H), 4.83 (d, J=9.3 Hz, 1H), 4.69 (br. s., 2H), 4.46 (br. s., 1H), 3.71-3.96 (m, 2H), 3.30-3.48 (m, 2H), 2.80-3.05 (m, 2H), 2.54 (s, 3H).

Sources & evidence

ORD record
ord-12d10f731c3b4c3f8caada824332fb56
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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