Diisopropylethylamine → 6-{1-[4-(Dimethylamino)butanoyl]-1,2,3,6-tetra-hydropyridin-4-yl}-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2375833Notes

Reaction equation

HRID 2375833 reaction equation
Cl.Cl.Cl.[S:4]1[C:8]2[CH:9]=[C:10]([NH:13][C:14]3[C:15]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=5)[NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1.Cl.[CH3:30][N:31]([CH3:38])[CH2:32][CH2:33][CH2:34][C:35](O)=[O:36].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:30][N:31]([CH3:38])[CH2:32][CH2:33][CH2:34][C:35]([N:26]1[CH2:25][CH:24]=[C:23]([C:21]2[NH:20][C:16]3[N:17]=[CH:18][N:19]=[C:14]([NH:13][C:10]4[CH:11]=[CH:12][C:7]5[N:6]=[CH:5][S:4][C:8]=5[CH:9]=4)[C:15]=3[CH:22]=2)[CH2:28][CH2:27]1)=[O:36]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 69274170Benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine trihydrochloride

Product 1

HCID 587099376-{1-[4-(Dimethylamino)butanoyl]-1,2,3,6-tetra-hydropyridin-4-yl}-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine trihydrochloride (50.0 mg, 0.11 mmol) in DMF (3 mL) was added 4-(dimethylamino)butyric acid hydrochloride (17 mg, 0.13 mmol), TBTU (42 mg, 0.13 mmol) and N,N-diisopropylethylamine (0.11 mL). The reaction mixture was left to stir at rt over the weekend. The crude mixture was concentrated in vacuo and purified via MDP, which afforded the title compound as a tan solid. MS (ES+): m/z: 461.99 (100) [MH+]. HPLC: tr=1.82 min (ZQ2000: polar—5 min). 1H NMR (400 MHz, DMSO-d6): δ=1.63-1.68 (m, 2H), 2.10 (s, 3H), 2.11 (s, 3H), 2.18-2.24 (m, 2H), 2.33-2.43 (m, 2H), 2.54-2.56 (m, 2H), 3.67-3.72 (m, 2H), 4.15 (bs, 1H), 4.21 (bs, 1H), 6.45 (s, 1H), 6.84 (d, J=6.4 Hz, 1H), 7.87 (dd, J=1.6, 8.8 Hz, 1H), 8.03 (d, J=8.8 Hz, 1H), 8.34 (s, 1H), 8.92 (s, 1H), 9.23 (s, 1H), 9.61 (s, 1H), 12.02 (d, J=11.2 Hz, 1H).

Workup

  1. waitThe reaction mixture was left
  2. concentrationThe crude mixture was concentrated in vacuo
  3. custompurified via MDP, which

Sources & evidence

ORD record
ord-5f955389e0914458b5d01e3df9f07ab7
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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