Hydrochloric Acid → HCID 131729463, compound

HRID 2370319Notes

Reaction equation

HRID 2370319 reaction equation
C(N1C2C=CC=C(C([O-])=O)C=2C(CNC2C3CCN(CC3)C2)=N1)C1C=CC=CC=1.C(N1C2C=CC=C(C([O-])=O)C=2C(CN[C@@H]2C3CCN(CC3)C2)=N1)C1C=CC=CC=1.[Li+].[CH2:60]([N:67]1[C:71]2[CH:72]=[N:73][CH:74]=[C:75]3[C:76](=[O:87])[C@@H:77]([CH:79]4[CH:84]5[CH2:85][CH2:86][N:81]([CH2:82][CH2:83]5)[CH2:80]4)[CH2:78][C:69]([C:70]=23)=[N:68]1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1.[ClH:88]>>[ClH:88].[CH2:60]([N:67]1[C:71]2[CH:72]=[N:73][CH:74]=[C:75]3[C:76](=[O:87])[C@@H:77]([CH:79]4[CH:84]5[CH2:83][CH2:82][N:81]([CH2:86][CH2:85]5)[CH2:80]4)[CH2:78][C:69]([C:70]=23)=[N:68]1)[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 66772458HCID 66772458, compoundHCID 66772796HCID 66772796, compound2×HCID 131729464HCID 131729464, compound

Product 1

HCID 131729463HCID 131729463, compound

Procedure

Following general procedure GP-G, 1-benzyl-3-((quinuclidin-3-ylamino)methyl)-1H-indazole-4-carboxylate was converted to lithium (R)-1-benzyl-3-((quinuclidin-3-ylamino)methyl)-1H-indazole-4-carboxylate: MS (ESI+) m/z 391 (M+H). Step D: Following general procedure CP-H, lithium (R)-1-benzyl-3-((quinuclidin-3-ylamino)methyl)-1H-indazole-4-carboxylate was converted to (R)-2-benzyl-7-(quinuclidin-3-yl)-7,8-dihydropyrazolo[3,4,5-de]isoquinolin-6(2H)-one, which was immediately treated with hydrochloric acid following general procedure GP-I to give (R)-2-benzyl-7-(quinuclidin-3-yl)-7,8-dihydropyrazolo[3,4,5-de]isoquinolin-6(2H)-one, hydrochloride salt as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.62 (d, J=4.0 Hz, 1H), 7.56-7.51 (m, 2H), 7.29-7.25 (m, 5H), 5.65 (s, 2H), 5.29 (d, J=8.5 Hz, 1H), 5.19 (d, J=8.5 Hz, 1H), 4.70 (t, J=9.5 Hz, 1H), 3.89-3.78 (m, 2H), 3.68-3.63 (m, 1H), 3.44-3.40 (m, 3H), 2.63 (br s, 1H), 2.44-2.38 (m, 1H), 2.18-2.11 (m, 2H), 2.05 (br s, 1H); MS (ESI+) m/z 373 (M+H); HPLC>99% (AUC), tR 14.38 min.

Sources & evidence

ORD record
ord-b0adaef5225d4090826f07ff5c95ba3d
Source dataset
uspto-grants-2014_04
Patent number
US08710047B2

Reaction notes

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